Benzoxaborole Compounds

ABSTRACT

Further the invention relates to novel compounds of the formula (I), compositions comprising them a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one azine of the formula I to act on plants, their seed and/or their habitat.

The present invention relates to benzoxaborole compounds and to theiruse as herbicides. The present invention also relates to agrochemicalcompositions for crop protection and to a method for controllingunwanted vegetation.

WO 2015/121442 describes bezoboroles of the formula I

and their microbiocidally activity.

WO 2014/149793 describes 1-hydroxybenzooxaboroles as atiparasiticagents.

WO 2011/049971 discloses boron-containing small molecules asantiprotozoal agents.

Bioorganic and Medicinal Chemistry Letters (2011), 21(7), 2048-2054describes synthesis and SAR of acyclic HCV NS3 protease inhibitors withnovel P4-benzoxaborole moieties.

WO 2011017125 describes trisubstituted benzoxaborole compounds asantibacterial agents, their preparation and use in the treatment ofbacterial infection.

US 20070286822 describes boron compounds for the treatment ofperiodontal disease such as infection involving bacteria, viruses, fungiand/or parasites.

WO 2007095638 describes boron-containing small molecules asanti-inflammatory agents.

An application as a herbicide of the above mentioned compounds is notmentioned in the cited state of the art documents.

It is therefore an object of the present invention to provide compoundshaving improved herbicidal action, in particular good herbicide activityat low application rates. Moreover, the herbicids should be sufficientlycompatible with crop plants for commercial utilization.

These and further objects are achieved by the use of benzoxabolecompounds of formula (I), defined below, and by their agriculturallysuitable salts.

Accordingly, the present invention relates to a use of compounds offormula (I)

wherein

-   -   X is O, NR⁷ or S, SO, SO₂;    -   Y is C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl where the        radicals are unsubstituted or substituted by 1, 2, 3, 4 or 5        identical or different substituents selected from the group        consisting of halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C(═O)O(C₁-C₆-alkyl) and phenyl        which is unsubstituted or substituted by halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl;    -   R¹ is selected from the group consisting of H and C₁-C₆-alkyl;    -   R² is selected from the group consisting of H and C₁-C₆-alkyl;    -   R³ is selected from the group consisting of H, halogen, OH, CN,        amino, NO₂, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,        C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,        (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,        (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, (C₁-C₆-alkoxy)-C₃-C₆-alkynyl,        where the aliphatic and cycloaliphatic parts of the        aforementioned radicals are unsubstituted, partly or completely        halogenated;    -   R⁴ is selected from the group consisting of H, halogen, OH, CN,        amino, NO₂, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,        C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,        (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,        (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, (C₁-C₆-alkoxy)-C₃-C₆-alkynyl,        where the aliphatic and cycloaliphatic parts of the        aforementioned radicals are unsubstituted, partly or completely        halogenated;    -   R⁵ is selected from the group consisting of H, halogen, OH, CN,        amino, NO₂, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl,        C₁-C₆-alkoxy, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy,        (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,        (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, (C₁-C₆-alkoxy)-C₃-C₆-alkynyl,        where the aliphatic and cycloaliphatic parts of the        aforementioned radicals are unsubstituted, partly or completely        halogenated;    -   R⁶ is selected from the group consisting of H, C₁-C₆-alkyl,        C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,        (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, (C₁-C₆-alkoxy)-C₃-C₆-alkynyl,        phenyl, phenyl-C₁-C₆-alkyl, where the aliphatic and        cycloaliphatic parts of the aforementioned radicals are        unsubstituted, partly or completely halogenated;    -   R⁷ is selected from the group consisting of H, C₁-C₆-alkyl,        C₃-C₆-alkenyl, C₃-C₆-alkynyl;    -   including their agriculturally acceptable salts for for        controlling unwanted vegetation.

The present invention also relates to the compounds of the formula (I)as defined in claim 1 with the proviso that

if R¹ and R² are H

R⁴ is not H, Cl and F; and

if R¹ or R² is CH₃

R⁴ is not H.

The present invention also relates to agrochemical compositionscomprising a herbicidal active amount of at least one compound (I) asdefined above and at least one inert liquid and/or solid carrier and, ifappropriate, at least one surface-active substances.

The present invention also relates to method for controlling unwantedvegetation which comprises allowing a herbicidally effective amount ofat least one compound of the formula I or of an agriculturally suitablesalt or N-oxide thereof as defined to act on plants, their seed and/ortheir habitat. Application can be done before, during and/or after,preferably during and/or after, the emergence of the unwanted plants.

Further embodiments of the present invention are evident from theclaims, the description and the examples. It is to be understood thatthe features mentioned above and still to be illustrated below of thesubject matter of the invention can be applied not only in thecombination given in each particular case but also in othercombinations, without leaving the scope of the invention.

As used herein, the terms “controlling” and “combating” are synonyms.

As used herein, the terms “undesirable vegetation”, “unwantedvegetation”, unwanted plants” and “harmful plants” are synonyms.

In the context of substituents, the term “one or more substitutents”means that the number of substituents is e.g. from 1 to 10, inparticular 1, 2, 3, 4, 5, 6, 7 or 8.

If the benzoxaborole compounds of formula (I) as described herein iscapable of forming geometrical isomers, for example E/Z isomers, theinvention relates to both the pure isomers and mixtures thereof.Likewise, the invention relates to the use of the pure pure isomers andto the use of their mixtures and to compositions containing the pureisomers or mixtures thereof.

If the benzoxaborole compounds of formula (I) as described herein haveone or more centres of chirality and, as a consequence, are present asenantiomers or diastereomers, the invention relates to both the pureenantiomers or diastereomers, and mixtures thereof. Likewise, theinvention relates to the use of the pure enantiomers or diastereomersand to the use of the mixtures thereof and to compositions containingthe pure enantiomers or diastereomers or mixtures thereof.

If the benzoxaborole compounds of formula (I) as described herein haveionizable functional groups, they can also be employed in the form oftheir agriculturally acceptable salts. Suitable are, in general, thesalts of those cations and the acid addition salts of those acids whosecations and anions, respectively, have no adverse effect on the activityof the active compounds.

Preferred cations are the ions of the alkali metals, preferably oflithium, sodium and potassium, of the alkaline earth metals, preferablyof calcium and magnesium, and of the transition metals, preferably ofmanganese, copper, zinc and iron, further ammonium and substitutedammonium in which one to four hydrogen atoms are replaced byC₁-C₄-alkyl, hydroxy-C₁-C₄-alkyl, (C₁-C₄-alkoxy)-C₁-C₄-alkyl,hydroxy-(C₁-C₄-alkoxy)-C₁-C₄-alkyl, phenyl or benzyl, preferablyammonium, methylammonium, isopropylammonium, dimethylammonium,diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium,tetradecylammonium, tetramethylammonium, tetraethylammonium,tetrabutylammonium, 2-hydroxyethyl-ammonium (olamine salt),2-(2-hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt),di(2-hydroxyeth-1-yl)-ammonium (diolamine salt),tris(2-hydroxyethyl)ammonium (trolamine salt),tris(2-hydroxypropyl)ammonium, benzyltrimethylammonium,benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt),furthermore phosphonium ions, sulfonium ions, preferablytri(C₁-C₄-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxoniumions, preferably tri(C₁-C₄-alkyl)sulfoxonium, and finally the salts ofpolybasic amines such as N,N-bis-(3-aminopropyl)methylamine anddiethylenetriamine.

Anions of useful acid addition salts are primarily chloride, bromide,fluoride, iodide, hydrogensulfate, methylsulfate, sulfate,dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate,hexafluorosilicate, hexafluorophosphate, benzoate and also the anions ofC₁-C₄-alkanoic acids, preferably formate, acetate, propionate andbutyrate.

Further embodiments of the present invention are evident from theclaims, the description and the examples. It is to be understood thatthe features mentioned above and still to be illustrated below of thesubject matter of the invention can be applied not only in thecombination given in each particular case but also in othercombinations, without leaving the scope of the invention.

The organic moieties mentioned in the definition of the variables, e.g.X, Y, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ are—like the term halogen—collectiveterms for individual enumerations of the individual group members. Theterm halogen denotes in each case fluorine, chlorine, bromine or iodine.All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkenyl, alkynyl,alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl,(alkyl)amino, di(alkyl)amino, alkoxyalkyl, alkoxyalkoxy, (alky)carbonyl,(alkoxy)carbonyl chains can be straight-chain or branched, the prefixC_(n)-C_(m) denoting in each case the possible number of carbon atoms inthe group. The same applies to composed radicals, such ascycloalkylalkyl and phenylalkyl.

-   -   Examples of such meanings are:    -   C₁-C₄-alkyl and also the C₁-C₄-alkyl moieties of C₁-C₄-alkoxy,        C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, (C₁-C₄-alkyl)carbonyl,        (C₁-C₄-alkyl)carbonyl, (C₁-C₄-alkoxy)carbonyl,        (C₁-C₄-alkyl)carbonyloxy, C₁-C₄-alkyoxy-C₁-C₄-alkyl,        C₃-C₆-cycloalkyl-C₁-C₄-alkyl, (C₁-C₄-alkylamino)carbonyl,        di(C₁-C₄-alkyl)aminocarbonyl, (C₁-C₄-alkylamino)sulfonyl,        di(C₁-C₄-alkyl)aminosulfonyl or phenyl-C₁-C₄-alkyl: for example        CH₃, C₂H₅, n-propyl, CH(CH₃)₂, n-butyl, CH(CH₃)—C₂H₅,        CH₂—CH(CH₃)₂ and C(CH₃)₃;    -   C₁-C₆-alkyl and also the C₁-C₆-alkyl moieties of C₁-C₆-alkoxy,        C₁-C₆-alkylthio, C₁-C₆-alkylsulfonyl, (C₁-C₆-alkyl)carbonyl,        (C₁-C₆-alkyl)carbonyl, (C₁-C₆-alkoxy)carbonyl,        (C₁-C₆-alkyl)carbonyloxy, C₁-C₆-alkyoxy-C₁-C₆-alkyl,        C₃-C₆-cycloalkyl-C₁-C₆-alkyl, phenyl(C₁-C₆-alkyl)aminocarbonyl,        (C₁-C₆-alkylamino)carbonyl, di(C₁-C₆-alkyl)aminocarbonyl,        (C₁-C₆-alkylamino)sulfonyl, di(C₁-C₆-alkyl)aminosulfonyl or        phenyl-C₁-C₆-alkyl: C₁-C₄-alkyl as mentioned above, and also,        for example, n-pentyl, 1-methylbutyl, 2-methylbutyl,        3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl,        1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,        2-methylpentyl, 3-methylpentyl, 4-methylpentyl,        1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,        2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,        1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,        1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or        1-ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl,        1-methylethyl, n-butyl, 1,1-dimethylethyl, n-pentyl or n-hexyl;    -   C₂-C₆-alkenyl and also the C₂-C₆-alkenyl moieties of        (C₁-C₆-alkoxy)-C₂-C₆-alkenyl: a linear or branched ethylenically        unsaturated hydrocarbon group having 2 to 6 carbon atoms and a        C═C-double bond in any position, such as ethenyl, 1-propenyl,        2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl,        1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,        2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl,        4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl,        3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl,        3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl,        3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,        1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl,        1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,        3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,        2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,        1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,        4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,        3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,        2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,        1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,        1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,        1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,        1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,        2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,        2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,        3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,        1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,        2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,        1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,        1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;    -   C₂-C₆-alkynyl and also the C₂-C₆-alkynyl moieties of        (C₁-C₆-alkoxy)-C₂-C₆-alkynyl: linear or branched unsaturated        hydrocarbon group having 2 to 6 carbon atoms and containing at        least one C—C-triple bond, such as ethynyl, 1-propynyl,        2-propynyl (propargyl), 1-butynyl, 2-butynyl, 3-butynyl,        1-methyl-2-propynyl and the like;    -   C₁-C₄-haloalkyl: a C₁-C₄-alkyl radical as mentioned above which        is partially or fully substituted by fluorine, chlorine, bromine        and/or iodine, for example, chloro-methyl, dichloromethyl,        trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,        chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,        bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl,        2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl,        2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,        2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,        2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,        3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,        2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,        2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,        3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,        heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,        1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,        4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl,        1,1,2,2,-tetrafluoroethyl and        1-trifluoromethyl-1,2,2,2-tetrafluoroethyl;    -   C₁-C₆-haloalkyl: C₁-C₄-haloalkyl as mentioned above, and also,        for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl,        5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl,        6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;    -   C₃-C₆-cycloalkyl: monocyclic saturated hydrocarbons having 3 to        6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and        cyclohexyl;    -   C₁-C₄-alkoxy: for example methoxy, ethoxy, propoxy,        1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy and        1,1-dimethylethoxy;    -   C₁-C₆-alkoxy and also the C₁-C₆-alkoxy moieties of        (C₁-C₆-alkoxy)carbonyl, (C₁-C₆-alkoxy)sulfonyl,        (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,        (C₁-C₆-alkoxy)-C₂-C₆-alkenyl, (C₁-C₆-alkoxy)-C₂-C₆-alkynyl:        C₁-C₄-alkoxy as mentioned above, and also, for example, pentoxy,        1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy,        1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy,        1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy,        3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy,        1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy,        2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,        2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,        1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;    -   C₁-C₄-haloalkoxy: a C₁-C₄-alkoxy radical as mentioned above        which is partially or fully substituted by fluorine, chlorine,        bromine and/or iodine, for example, chloro-methoxy,        dichloromethoxy, trichloromethoxy, fluoromethoxy,        difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy,        dichlorofluoromethoxy, chlorodifluoromethoxy2-fluoroethoxy,        2-chloroethoxy, 2-bromoethxoy, 2,2-difluoroethoxy,        2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,        2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,        2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,        3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy,        2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy,        3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,        2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,        1-(fluoromethyl)-2-fluoroethoxy, 4-fluorobutoxy,        nonafluorobutoxy, 1,1,2,2,-tetrafluoroethoxy and        1-trifluoromethyl-1,2,2,2-tetrafluoroethoxy;    -   C₁-C₆-haloalkoxy: C₁-C₄-alkoxy as mentioned above:        C₁-C₄-haloalkoxy as mentioned above, and also, for example,        5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl,        undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl,        6-iodohexyl and dodecafluorohexyl;    -   C₂-C₆-alkenyloxy: C₂-C₆-alkenyl as defined above, which is bound        via an oxygen atom, such as ethenyloxy (vinyloxy),        1-propenyloxy, 2-propenyloxy (allyloxy), 1-butenyloxy,        2-butenyloxy, 3-butenyloxy 1-methyl-2-propenyloxy and the like;    -   C₂-C₆-alkynyloxy: C₂-C₆-alkynyl as defined above, which is bound        via an oxygen atom, such as ethynyloxy, 1-propynyl,        2-propynyloxy (propargyloxy), 1-butynyloxy, 2-butynyloxy,        3-butynyloxy 1-methyl-2-propynyloxy and the like;    -   (C₁-C₆-alkoxy)-C₁-C₆-alkyl: C₁-C₆-alkyl, in particular        C₁-C₄-alkyl as defined above, such as methyl, ethyl or        isopropyl, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy        as defined above, examples including methoxymethyl,        ethoxymethyl, n-propoxymethyl, butoxymethyl, 1-methoxyethyl,        1-ethoxyethyl, 1-(n-propoxy)ethyl, 1-butoxyethyl,        2-methoxyethyl, 2-ethoxyethyl, 2-(n-propoxy)ethyl,        2-butoxyethyl, 2-methoxypropyl, 2-ethoxypropyl,        2-(n-propoxy)propyl, 2-butoxypropyl;    -   (C₁-C₆-alkoxy)-C₁-C₆-alkoxy: C₁-C₆-alkoxy, in particular        C₁-C₄-alkoxy as defined above, such as methoxy or ethoxy,        wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy as defined        above, examples including methoxymethoxy, ethoxymethoxy,        n-propoxymethoxy, butoxymethoxy, 2-methoxyethoxy,        2-ethoxyethoxy, 2-(n-propoxy)ethoxy and 2-butoxyethoxy;    -   (C₁-C₆-alkoxy)-C₂-C₆-alkenyl: C₂-C₆-alkenyl, in particular        C₂-C₄-alkenyl as defined above, such as ethenyl, propenyl,        1-butenyl or 2-butenyl, wherein 1 hydrogen atom is replaced by        C₁-C₆-alkoxy as defined above;    -   (C₁-C₆-alkoxy)-C₂-C₆-alkynyl: C₂-C₆-alkynyl, in particular        C₂-C₄-alkynyl as defined above, such as ethynyl, propynyl or        2-butynyl, wherein 1 hydrogen atom is replaced by C₁-C₆-alkoxy        as defined above;    -   phenyl-C₁-C₆-alkyl: C₁-C₆-alkyl, in particular C₁-C₄-alkyl as        defined above, such as methyl or ethyl, wherein 1 hydrogen atom        is replaced by phenyl, examples including benzyl, 1-phenylethyl,        2-phenylethyl, 1-phenylpropyl, 2-phenylpropyl,        1-phenyl-1-methylethyl etc.

The preferred embodiments of the invention mentioned herein below haveto be understood as being preferred either independently from each otheror in combination with one another.

Particular groups of embodiments of the invention relate to thosebenzoxaboroles of formula (I), wherein the variables X, Y, R¹, R², R³,R⁴, R⁵, R⁶ and R⁷ either independently of one another or in combinationwith one another, have the following meanings:

Particular groups of embodiments relate to the benzoxaborole compoundsof formula (I), wherein

X is is O, NR⁷ or S, SO, SO₂.

In this context

-   R⁷ is in particular selected from the group consisting of H,    C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, more particularly    selected from the group consisting of H and C₁-C₆-alkyl, even more    particularly selected from the group consisting of H, methyl and    ethyl; more particular X is O or NR⁷;    -   even more particular X is O.

Further particular groups of embodiment relate to the benzoxaborolecompound of formula (I), wherein:

-   Y is C₁-C₆-alkyl or C₃-C₆-alkenyl which are unsubstituted or    substituted by 1 or 2, identical substituents selected from the    group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,    C₁-C₆-haloalkoxy, C(═O)O(C₁-C₆-alkyl) and phenyl which is    unsubstituted or substituted by halogen, C₁-C₆-alkyl,    C₁-C₆-haloalkyl;    -   preferably is C₁-C₆-alkyl which is unsubstituted or substituted        by 1 or 2, identical substituents selected from the group        consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,        C₁-C₆-haloalkoxy, C(═O)O(C₁-C₆-alkyl) and phenyl which is        unsubstituted or substituted by halogen, C₁-C₆-alkyl,        C₁-C₆-haloalkyl;    -   in particular is —CH₂— which is unsubstituted or substituted by        1 or 2, identical substituents selected from the group        consisting of C₁-C₆-alkyl, C₁-C₆-alkoxy, C(═O)O(C₁-C₆-alkyl) and        phenyl;    -   more particularly in particular is —CH₂— which is unsubstituted        or substituted by 1 or 2, identical substituents selected from        the group consisting of CH₃, CH₂CH₃, C(═O)(OCH₃), OCH₃ and        phenyl;    -   especially —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—, —CH(CH₃)—, —C(CH₃)₂—,        —CH(CH₂CH₃)—, —CH(OCH₃)—, —CH(C(═O)(OCH₃)—, —CH(phenyl).

Further particular groups of embodiment relate to the benzoxaborolecompound of formula (I), wherein:

-   R¹ is selected from the group consisting of H and C₁-C₆-alkyl;    -   preferably, H, C₁-C₄-alkyl;    -   in particular H, CH₃, CH₂CH₃;    -   especially CH₃;    -   more especially H.

Further particular groups of embodiment relate to the benzoxaborolecompound of formula (I), wherein:

-   R² is selected from the group consisting of H and C₁-C₆-alkyl;    -   preferably, H, C₁-C₄-alkyl;    -   in particular H, CH₃, CH₂CH₃;    -   especially H.

Further particular groups of embodiments relate to the benzoxaborolecompounds of formula (I), wherein;

-   R³ is selected from the group consisting of H, halogen, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂—(C₁-C₆-alkoxy)-C₁-C₆-alkyl,    (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic    parts of the aforementioned radicals are unsubstituted, partly or    completely halogenated; preferably H, halogen, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂—(C₁-C₆-alkoxy)-C₁-C₆-alkyl,    (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic    parts of the aforementioned radicals are unsubstituted, partly or    completely halogenated;    -   in particular H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl;    -   more particularly H, C, F, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   even more particularly H, C, F, CH₃;    -   especially H.-   R⁴ is selected from the group consisting of H, halogen, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂—(C₁-C₆-alkoxy)-C₁-C₆-alkyl,    (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic    parts of the aforementioned radicals are unsubstituted, partly or    completely halogenated;    -   preferably H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,        C₂—(C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy,        where the aliphatic and cycloaliphatic parts of the        aforementioned radicals are unsubstituted, partly or completely        halogenated;    -   in particular H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl;    -   more particularly H, C, F, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   even more particularly H, C, F, CH₃;    -   especially H, Cl, F.-   R⁵ is selected from the group consisting of H, halogen, C₁-C₆-alkyl,    C₁-C₆-alkoxy, C₂—(C₁-C₆-alkoxy)-C₁-C₆-alkyl,    (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where the aliphatic and cycloaliphatic    parts of the aforementioned radicals are unsubstituted, partly or    completely halogenated;    -   preferably H, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,        (C₁-C₆-alkoxy)-C₁-C₆-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkoxy, where        the aliphatic and cycloaliphatic parts of the aforementioned        radicals are unsubstituted, partly or completely halogenated;    -   in particular H, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl;    -   more particularly H, C, F, C₁-C₄-alkyl, C₁-C₄-haloalkyl;    -   even more particularly H, C, F, CH₃;    -   especially H, Cl, F.-   R⁶ is selected from the group consisting of H, C₁-C₆-alkyl,    (C₁-C₆-alkoxy)-C₁-C₆-alkyl, phenyl, phenyl-C₁-C₆-alkyl, where the    aliphatic and cycloaliphatic parts of the aforementioned radicals    are unsubstituted, partly or completely halogenated;    -   preferably H, halogen, C₁-C₄-alkyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,        where the aliphatic and cycloaliphatic parts of the        aforementioned radicals are unsubstituted, partly or completely        halogenated;    -   in particular H, C₁-C₆-alkyl;    -   more particularly H, C₁-C₄-alkyl;    -   even more particularly H, CH₃, CH₂CH₃;    -   especially H, CH₃.

Particularly preferred are the benzoxaborole compounds of formula (I)wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is hydrogen;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is not H;    -   R⁵ is as defined above; and    -   R⁶ is H.

More particularly preferred are the benzoxaborole compounds of formula(I) wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is hydrogen;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is selected from the group consisting of halogen, C₁-C₆-alkyl        and C₁-C₆-haloalkyl;    -   R⁵ is as defined above; and    -   R⁶ is H.

Even more particularly preferred are the benzoxaborole compounds offormula (I) wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is hydrogen;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is selected from the group consisting of halogen and        C₁-C₆-alkyl;    -   R⁵ is as defined above; and    -   R⁶ is H.

Especially preferred are the benzoxaborole compounds of formula (I)wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is hydrogen;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is Cl or F;    -   R⁵ is as defined above; and    -   R⁶ is H.

Further, particularly preferred are the benzoxaborole compounds offormula (I) wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is CH₃;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is not H;    -   R⁵ is as defined above; and    -   R⁶ is H.

More particularly preferred are the benzoxaborole compounds of formula(I) wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is CH₃;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is selected from the group consisting of halogen, C₁-C₆-alkyl        and C₁-C₆-haloalkyl;    -   R⁵ is as defined above; and    -   R⁶ is H.

Even more particularly preferred are the benzoxaborole compounds offormula (I) wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is CH₃;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is selected from the group consisting of halogen and        C₁-C₆-alkyl;    -   R⁵ is as defined above; and    -   R⁶ is H.

Especially preferred are the benzoxaborole compounds of formula (I)wherein

-   -   A is O,    -   Y is as defined above;    -   R¹ is CH₃;    -   R² is hydrogen;    -   R³ is as defined above;    -   R⁴ is Cl or F;    -   R⁵ is as defined above; and    -   R⁶ is H.

Particular preference is given to benzoxaborole compounds of formula(La), (I.b) and (I.c), which corresponds to benzoxaboroles of formula(I) wherein X is O, R¹ and R² is hydrogen, R⁶ is H. CH, and CH₂CH₃respectively and R³, R⁴, R⁵ and Y are defined in table A.

-   Table A-1: Compounds of formula (I.a), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.a.A-1.1-I.a.A-1.192).-   Table A-2: Compounds of formula (I.b), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.b.A-2.1-I.b.A-2.192).-   Table A-3: Compounds of formula (I.c), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.c.A-3.1-I.c.A-3.192).-   Table A-4: Compounds of formula (I.d), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.d.A-4.1-I.d.A-4.192).-   Table A-5: Compounds of formula (I.e), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.e.A-5.1-I.e.A-5.192).-   Table A-6: Compounds of formula (If), where R³, R⁴, R⁵ and Y are    defined the rows of table A (I.f.A-6.1-I.f.A-6.192).

TABLE A no. R³ R⁴ R⁵ Y 1. H H H —CH₂— 2. F H H —CH₂— 3. Cl H H —CH₂— 4.CH₃ H H —CH₂— 5. H F H —CH₂— 6. F F H —CH₂— 7. Cl F H —CH₂— 8. CH₃ F H—CH₂— 9. H Cl H —CH₂— 10. F Cl H —CH₂— 11. Cl Cl H —CH₂— 12. CH₃ Cl H—CH₂— 13. H CH₃ H —CH₂— 14. F CH₃ H —CH₂— 15. Cl CH₃ H —CH₂— 16. CH₃ CH₃H —CH₂— 17. H H F —CH₂— 18. F H F —CH₂— 19. Cl H F —CH₂— 20. CH₃ H F—CH₂— 21. H F F —CH₂— 22. F F F —CH₂— 23. Cl F F —CH₂— 24. CH₃ F F —CH₂—25. H Cl F —CH₂— 26. F Cl F —CH₂— 27. Cl Cl F —CH₂— 28. CH₃ Cl F —CH₂—29. H CH₃ F —CH₂— 30. F CH₃ F —CH₂— 31. Cl CH₃ F —CH₂— 32. CH₃ CH₃ F—CH₂— 33. H H Cl —CH₂— 34. F H Cl —CH₂— 35. Cl H Cl —CH₂— 36. CH₃ H Cl—CH₂— 37. H F Cl —CH₂— 38. F F Cl —CH₂— 39. Cl F Cl —CH₂— 40. CH₃ F Cl—CH₂— 41. H Cl Cl —CH₂— 42. F Cl Cl —CH₂— 43. Cl Cl Cl —CH₂— 44. CH₃ ClCl —CH₂— 45. H CH₃ Cl —CH₂— 46. F CH₃ Cl —CH₂— 47. Cl CH₃ Cl —CH₂— 48.CH₃ CH₃ Cl —CH₂— 49. H H CH₃ —CH₂— 50. F H CH₃ —CH₂— 51. Cl H CH₃ —CH₂—52. CH₃ H CH₃ —CH₂— 53. H F CH₃ —CH₂— 54. F F CH₃ —CH₂— 55. Cl F CH₃—CH₂— 56. CH₃ F CH₃ —CH₂— 57. H Cl CH₃ —CH₂— 58. F Cl CH₃ —CH₂— 59. ClCl CH₃ —CH₂— 60. CH₃ Cl CH₃ —CH₂— 61. H CH₃ CH₃ —CH₂— 62. F CH₃ CH₃—CH₂— 63. Cl CH₃ CH₃ —CH₂— 64. CH₃ CH₃ CH₃ —CH₂— 65. H H H —CH(CH₃)— 66.F H H —CH(CH₃)— 67. Cl H H —CH(CH₃)— 68. CH₃ H H —CH(CH₃)— 69. H F H—CH(CH₃)— 70. F F H —CH(CH₃)— 71. Cl F H —CH(CH₃)— 72. CH₃ F H —CH(CH₃)—73. H Cl H —CH(CH₃)— 74. F Cl H —CH(CH₃)— 75. Cl Cl H —CH(CH₃)— 76. CH₃Cl H —CH(CH₃)— 77. H CH₃ H —CH(CH₃)— 78. F CH₃ H —CH(CH₃)— 79. Cl CH₃ H—CH(CH₃)— 80. CH₃ CH₃ H —CH(CH₃)— 81. H H F —CH(CH₃)— 82. F H F—CH(CH₃)— 83. Cl H F —CH(CH₃)— 84. CH₃ H F —CH(CH₃)— 85. H F F —CH(CH₃)—86. F F F —CH(CH₃)— 87. Cl F F —CH(CH₃)— 88. CH₃ F F —CH(CH₃)— 89. H ClF —CH(CH₃)— 90. F Cl F —CH(CH₃)— 91. Cl Cl F —CH(CH₃)— 92. CH₃ Cl F—CH(CH₃)— 93. H CH₃ F —CH(CH₃)— 94. F CH₃ F —CH(CH₃)— 95. Cl CH₃ F—CH(CH₃)— 96. CH₃ CH₃ F —CH(CH₃)— 97. H H Cl —CH(CH₃)— 98. F H Cl—CH(CH₃)— 99. Cl H Cl —CH(CH₃)— 100. CH₃ H Cl —CH(CH₃)— 101. H F Cl—CH(CH₃)— 102. F F Cl —CH(CH₃)— 103. Cl F Cl —CH(CH₃)— 104. CH₃ F Cl—CH(CH₃)— 105. H Cl Cl —CH(CH₃)— 106. F Cl Cl —CH(CH₃)— 107. Cl Cl Cl—CH(CH₃)— 108. CH₃ Cl Cl —CH(CH₃)— 109. H CH₃ Cl —CH(CH₃)— 110. F CH₃ Cl—CH(CH₃)— 111. Cl CH₃ Cl —CH(CH₃)— 112. CH₃ CH₃ Cl —CH(CH₃)— 113. H HCH₃ —CH(CH₃)— 114. F H CH₃ —CH(CH₃)— 115. Cl H CH₃ —CH(CH₃)— 116. CH₃ HCH₃ —CH(CH₃)— 117. H F CH₃ —CH(CH₃)— 118. F F CH₃ —CH(CH₃)— 119. Cl FCH₃ —CH(CH₃)— 120. CH₃ F CH₃ —CH(CH₃)— 121. H Cl CH₃ —CH(CH₃)— 122. F ClCH₃ —CH(CH₃)— 123. Cl Cl CH₃ —CH(CH₃)— 124. CH₃ Cl CH₃ —CH(CH₃)— 125. HCH₃ CH₃ —CH(CH₃)— 126. F CH₃ CH₃ —CH(CH₃)— 127. Cl CH₃ CH₃ —CH(CH₃)—128. CH₃ CH₃ CH₃ —CH(CH₃)— 129. H H H —CH(OCH₃)— 130. F H H —CH(OCH₃)—131. Cl H H —CH(OCH₃)— 132. CH₃ H H —CH(OCH₃)— 133. H F H —CH(OCH₃)—134. F F H —CH(OCH₃)— 135. Cl F H —CH(OCH₃)— 136. CH₃ F H —CH(OCH₃)—137. H Cl H —CH(OCH₃)— 138. F Cl H —CH(OCH₃)— 139. Cl Cl H —CH(OCH₃)—140. CH₃ Cl H —CH(OCH₃)— 141. H CH₃ H —CH(OCH₃)— 142. F CH₃ H —CH(OCH₃)—143. Cl CH₃ H —CH(OCH₃)— 144. CH₃ CH₃ H —CH(OCH₃)— 145. H H F —CH(OCH₃)—146. F H F —CH(OCH₃)— 147. Cl H F —CH(OCH₃)— 148. CH₃ H F —CH(OCH₃)—149. H F F —CH(OCH₃)— 150. F F F —CH(OCH₃)— 151. Cl F F —CH(OCH₃)— 152.CH₃ F F —CH(OCH₃)— 153. H Cl F —CH(OCH₃)— 154. F Cl F —CH(OCH₃)— 155. ClCl F —CH(OCH₃)— 156. CH₃ Cl F —CH(OCH₃)— 157. H CH₃ F —CH(OCH₃)— 158. FCH₃ F —CH(OCH₃)— 159. Cl CH₃ F —CH(OCH₃)— 160. CH₃ CH₃ F —CH(OCH₃)— 161.H H Cl —CH(OCH₃)— 162. F H Cl —CH(OCH₃)— 163. Cl H Cl —CH(OCH₃)— 164.CH₃ H Cl —CH(OCH₃)— 165. H F Cl —CH(OCH₃)— 166. F F Cl —CH(OCH₃)— 167.Cl F Cl —CH(OCH₃)— 168. CH₃ F Cl —CH(OCH₃)— 169. H Cl Cl —CH(OCH₃)— 170.F Cl Cl —CH(OCH₃)— 171. Cl Cl Cl —CH(OCH₃)— 172. CH₃ Cl Cl —CH(OCH₃)—173. H CH₃ Cl —CH(OCH₃)— 174. F CH₃ Cl —CH(OCH₃)— 175. Cl CH₃ Cl—CH(OCH₃)— 176. CH₃ CH₃ Cl —CH(OCH₃)— 177. H H CH₃ —CH(OCH₃)— 178. F HCH₃ —CH(OCH₃)— 179. Cl H CH₃ —CH(OCH₃)— 180. CH₃ H CH₃ —CH(OCH₃)— 181. HF CH₃ —CH(OCH₃)— 182. F F CH₃ —CH(OCH₃)— 183. Cl F CH₃ —CH(OCH₃)— 184.CH₃ F CH₃ —CH(OCH₃)— 185. H Cl CH₃ —CH(OCH₃)— 186. F Cl CH₃ —CH(OCH₃)—187. Cl Cl CH₃ —CH(OCH₃)— 188. CH₃ Cl CH₃ —CH(OCH₃)— 189. H CH₃ CH₃—CH(OCH₃)— 190. F CH₃ CH₃ —CH(OCH₃)— 191. Cl CH₃ CH₃ —CH(OCH₃)— 192. CH₃CH₃ CH₃ —CH(OCH₃)—

The benzoxaborole compounds of formula (I) according to the inventioncan be prepared by standard processes of organic chemistry, for exampleby the following processes:

The benzoxaborole compounds of formula (I), wherein X is O, NH, NR⁷ andSand Y, R³, R⁴, R⁵ and R⁶ are as defined above, can be prepared byreacting benzoxaborol of formula (IIA) with a halogenated ester offormula (III) in the presence of a base as depicted in the followingscheme 1:

The reaction of the benzoxaborol of formula (II) with the ester offormula (III) is usually carried out at temperatures in the range roomtemperature in an inert organic solvent (Ding, Dazhong et al, Journal ofMedicinal Chemistry, 54(5), 1276-1287; 2011).

The reaction can be carried out at atmospheric pressure or underelevated pressure, if appropriate, under an inert gas, continuously orbatchwise.

In one embodiment of the process according to the invention, thebenzoxaborol of formula (II) with the ester of formula (III) are used inequimolar amounts.

In another embodiment of the process according to the invention, theester of formula (III) are used in excess with regard to thebenzoxaborol of formula (II).

Preferably the molar ratio of the ester of formula (III) to thebenzoxaborol of formula (II) is in the range from 2:1 to 1:1, preferably1.5:1 to 1:1, especially preferred 1.2:1.

The reaction of the benzoxaborol of formula (II) with the ester offormula (III) is usually carried out in an organic solvent. Suitable inprinciple are all solvents which are capable of dissolving thebenzoxaborol of formula (II) and the esters of formula (III) at leastpartly and preferably fully under reaction conditions. Examples ofsuitable solvents are aliphatic hydrocarbons such as pentane, hexane,cyclohexane, nitromethane and mixtures of C₅-C₈-alkanes, aromatichydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m-and p-xylene, halogenated hydrocarbons such as dichloromethane,1,2-dichloroethane, chloroform, carbon tetrachloride and chlorobenzene,ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether(TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethylacetate and butyl acetate; nitriles such as acetonitrile andpropionitrile, as well as dipolar aprotic solvents such as sulfolane,dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide(DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N′-dimethylpropyleneurea (DMPU), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone(NMP). Preferred solvents is DMF as defined above. The term solvent asused herein also includes mixtures of two or more of the abovecompounds.

The reaction of the the benzoxaborol of formula (II) and the esters offormula (III) is usually carried out in the presence of a base. Examplesof suitable bases include metal-containing bases and nitrogen-containingbases. Examples of suitable metal-containing bases are inorganiccompounds such as alkali metal and alkaline earth metal hydroxides, andother metal hydroxides, such as lithium hydroxide, sodium hydroxide,potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminumhydroxide; alkali metal and alkaline earth metal oxide, and other metaloxides, such as lithium oxide, sodium oxide, potassium oxide, magnesiumoxide, calcium oxide and magnesium oxide, iron oxide, silver oxide;alkali metal and alkaline earth metal hydrides such as lithium hydride,sodium hydride, potassium hydride and calcium hydride, alkali metal andalkaline earth metal formates, acetates and other metal salts ofcarboxylic acids, such as sodium formate, sodium benzoate, lithiumacetate, sodium acetate, potassium acetate, magnesium acetate, andcalcium acetate; alkali metal and alkaline earth metal carbonates suchas lithium carbonate, sodium carbonate, potassium carbonate, magnesiumcarbonate, and calcium carbonate, as well as alkali metal hydrogencarbonates (bicarbonates) such as lithium hydrogen carbonate, sodiumhydrogen carbonate, potassium hydrogen carbonate; alkali metal andalkaline earth metal phosphates such as sodium phosphate, potassiumphosphate and calcium phosphate; alkali metal and alkaline earth metalalkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide,potassium tert-butoxide, potassium tert-pentoxide anddimethoxymagnesium; and furthermore organic bases, such as tertiaryamines such as tri-C₁-C₆-alkylamines, for example triethylamine,trimethylamine, N-ethyldiisopropylamine, and N-methylpiperidine,pyridine, substituted pyridines such as collidine, lutidine,N-methylmorpholine and also bicyclic amines such as1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or1,5-diazabicyclo[4.3.0]non-5-ene (DBN). Preferred bases are alkali metaland alkaline earth metal alkoxides as defined above. The term base asused herein also includes mixtures of two or more, preferably two of theabove compounds.

Particular preference is given to the use of one base. The bases can beused in excess, preferably from 1 to 10, especially preferred from 2 to4 base equivalents based on the benzoxaborol of formula (II), and theymay also be used as the solvent.

The end of the reaction can easily be determined by the skilled workerby means of routine methods.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if appropriate,chromatographic purification of the crude product.

The benzoxaborol of formula (II) and the esters of formula (III) usedfor the preparation of benzoxaborole compounds of formula (I) arecommercially available and/or can be prepared by analogy to knownliterature (WO 2014149793, Li, Xianfeng et al, Bioorganic & MedicinalChemistry Letters, 21(7), 2048-2054; 2011, WO2007078340). Thebenzoxaborole compounds of formula (I), wherein X is SO and SO₂ and Y,R³, R⁴, R⁵ and R⁶ are as defined above, can be prepared by oxidation ofthe compound of the formula (I) wherein X is S and Y, R³, R⁴, R⁵ and R⁶as depicted in the following scheme 2:

The oxidation reaction is usually carried out at temperatures in therange between 0° C. and 100° C. (Medicinal Chemistry Letters, 1(4),165-169: 2010).

The reaction can be carried out at atmospheric pressure or underelevated pressure, if appropriate, under an inert gas, continuously orbatchwise.

In one embodiment of the process according to the invention, thecompound of the formula (I) with the oxidant are used in equimolaramounts.

In another embodiment of the process according to the invention, theoxidant is used in excess with regard to the compound of formula (I).

Preferably the molar ratio of the oxidant to the compound of formula (I)is in the range from 5:1 to 1:1, preferably 3:1 to 1:1, especiallypreferred 1.5:1.

The preferably oxidant is H₂O₂, NaIO₄, peracetic acid or MCPBA,especially H₂O₂.

The oxidation reaction is usually carried out in water or alkohols assolvent.

The end of the reaction can easily be determined by the skilled workerby means of routine methods.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, separation of the phases and, if appropriate,chromatographic purification of the crude product.

The compounds of formula (I) have herbicidal activity. Therefore, theycan be used for controlling unwanted or undesired plants or vegetation.They can also be used in a method for controlling unwanted or undesiredplants or vegetation, which method comprises allowing at least onecompound of formula (I) or a salt thereof to act on plants, theirenvironment or on seed. In order to allow the compound of formula (I) ora salt thereof to act on plants, their environment or on seed thecompounds of the invention are applied to the plants, their environmentor to the seed of said plants.

To widen the spectrum of action and to achieve synergistic effects, thebenzoxaborole compounds of formula (I) may be mixed with a large numberof representatives of other herbicidal or growth-regulating activeingredient groups and then applied concomitantly.

Suitable components for mixtures are, for example, herbicides from theclasses of the acetamides, amides, aryloxyphenoxypropionates,benzamides, benzofuran, benzoic acids, benzothiadiazinones,bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids,cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether,glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles,N-phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides,phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles,phenylpyrazolines, phenylpyridazines, phosphinic acids,phosphoroamidates, phosphorodithioates, phthalamates, pyrazoles,pyridazinones, pyridines, pyridinecarboxylic acids,pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates,quinolinecarboxylic acids, semicarbazones,sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones,thiadiazoles, thiocarbamates, triazines, triazinones, triazoles,triazolinones, triazolocarboxamides, triazolopyrimidines, triketones,uracils, ureas.

The invention also relates to combinations of benzoxaborole compounds offormula (I) with at least one further herbicide B and/or at least onesafener C).

The further herbicidal compound B (component B) is in particularselected from the herbicides of class b1) to b15):

-   -   b1) lipid biosynthesis inhibitors;    -   b2) acetolactate synthase inhibitors (ALS inhibitors);    -   b3) photosynthesis inhibitors;    -   b4) protoporphyrinogen-IX oxidase inhibitors,    -   b5) bleacher herbicides;    -   b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP        inhibitors);    -   b7) glutamine synthetase inhibitors;    -   b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);    -   b9) mitosis inhibitors;    -   b10) inhibitors of the synthesis of very long chain fatty acids        (VLCFA inhibitors);    -   b11) cellulose biosynthesis inhibitors;    -   b12) decoupler herbicides;    -   b13) auxinic herbicides;    -   b14) auxin transport inhibitors; and    -   b15) other herbicides selected from the group consisting of        bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin,        cumyluron, dalapon, dazomet, difenzoquat,        difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and        its salts, etobenzanid, flamprop, flamprop-isopropyl,        flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl,        flurenol, flurenol-butyl, flurprimidol, fosamine,        fosamine-ammonium, indanofan, indaziflam, maleic hydrazide,        mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide,        methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,        oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine,        triaziflam, tridiphane and        6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS        499223-49-3) and its salts and esters:

including their agriculturally acceptable salts or derivatives such asethers, esters or amides. Preference is given to those compositionsaccording to the present invention comprising at least one herbicide Bselected from herbicides of class b1, b6, b9, b10 and b11.

Examples of herbicides B which can be used in combination with thecompounds of formula (I) according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim,clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop,cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop,fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop,fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop,haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden,profoxydim, propaquizafop, quizalofop, quizalofop-ethyl,quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,

4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-72-6);4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-45-3);4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione(CAS 1312340-84-3);5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312337-48-6);5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312340-82-1);5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1033760-55-2);4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1);4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicidessuch as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC,esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate,prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron,bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron,cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl,ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron,halosulfuron-methyl, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl,nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron,primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron,pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl,sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron,tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron,triflusulfuron-methyl and tritosulfuron,

imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox,imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidineherbicides and sulfonanilides such as cloransulam, cloransulam-methyl,diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfanand pyroxsulam,

pyrimidinylbenzoates such as bispyribac, bispyribac-sodium,pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac,pyrithiobac-sodium,4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid-1-methylethyl ester (CAS 420138-41-6),4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoicacid propyl ester (CAS 420138-40-5),N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine(CAS 420138-01-8),

sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone,flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium,thiencarbazone and thiencarbazone-methyl; and triafamone;

among these, a preferred embodiment of the invention relates to thosecompositions comprising at least one imidazolinone herbicide;

b3) from the group of the photosynthesis inhibitors:

amicarbazone, inhibitors of the photosystem II, e.g. triazineherbicides, including of chlorotriazine, triazinones, triazindiones,methylthiotriazines and pyridazinones such as ametryn, atrazine,chloridazone, cyanazine, desmetryn, dimethametryn, hexazinone,metribuzin, prometon, prometryn, propazine, simazine, simetryn,terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such aschlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron,fluometuron, isoproturon, isouron, linuron, metamitron,methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon,siduron, tebuthiuron and thiadiazuron, phenyl carbamates such asdesmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrileherbicides such as bromofenoxim, bromoxynil and its salts and esters,ioxynil and its salts and esters, uraciles such as bromacil, lenacil andterbacil, and bentazon and bentazon-sodium, pyridate, pyridafol,pentanochlor and propanil and inhibitors of the photosystem I such asdiquat, diquat-dibromide, paraquat, paraquat-dichloride andparaquat-dimetilsulfate. Among these, a preferred embodiment of theinvention relates to those compositions comprising at least one arylurea herbicide. Among these, likewise a preferred embodiment of theinvention relates to those compositions comprising at least one triazineherbicide. Among these, likewise a preferred embodiment of the inventionrelates to those compositions comprising at least one nitrile herbicide;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone,benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl,flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen,halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone,profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil,sulfentrazone, thidiazimin, tiafenacil, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6; S-3100),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione(CAS 1258836-72-4),2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione,1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione,methyl(E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoate[CAS 948893-00-3], and3-[7-Chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione(CAS 212754-02-4);

b5) from the group of the bleacher herbicides:

PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone,flurtamone, norflurazon, picolinafen, and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, clomazone,fenquintrione, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate,pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone andbicyclopyrone,2-[(2,4-Dichlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone, CAS81777-95-9), bleacher, unknown target: aclonifen, amitrole, clomazone,and flumeturon;

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium, glyposate-potassium andglyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-Pand glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitosis inhibitors:

compounds of group K1: dinitroanilines such as benfluralin, butralin,dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin,prodiamine and trifluralin, phosphoramidates such as amiprophos,amiprophos-methyl, and butamiphos, benzoic acid herbicides such aschlorthal, chlorthal-dimethyl, pyridines such as dithiopyr andthiazopyr, benzamides such as propyzamide and tebutam; compounds ofgroup K2: chlorpropham, propham and carbetamide, among these, compoundsof group K1, in particular dinitroanilines are preferred;

b10) from the group of the VLCFA inhibitors:

chloroacetamides such as acetochlor, alachlor, butachlor, dimethachlor,dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S,pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor,oxyacetanilides such as flufenacet and mefenacet, acetanilides such asdiphenamid, naproanilide, napropamide and napropamide-M, tetrazolinonessuch fentrazamide, and other herbicides such as anilofos, cafenstrole,fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and

among the VLCFA inhibitors, preference is given to chloroacetamides andoxyacetamides;

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam, isoxaben and1-Cyclohexyl-5-pentafluorphenyloxy-1⁴-[1,2,4,6]thiatriazin-3-ylamine;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxinic herbicides:

2,4-D and its salts and esters such as clacyfos, 2,4-DB and its saltsand esters, aminocyclopyrachlor and its salts and esters, aminopyralidand its salts such as aminopyralid-dimethylammonium,aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin,benazolin-ethyl, chloramben and its salts and esters, clomeprop,clopyralid and its salts and esters, dicamba and its salts and esters,dichlorprop and its salts and esters, dichlorprop-P and its salts andesters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifenand its salts and esters (CAS 943832-60-8), florpyrauxifen-benzyl (CAS1390661-72-9); MCPA and its salts and esters, MCPA-thioethyl, MCPB andits salts and esters, mecoprop and its salts and esters, mecoprop-P andits salts and esters, picloram and its salts and esters, quinclorac,quinmerac, TBA (2,3,6) and its salts and esters and triclopyr and itssalts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr,diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol,chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat,difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and itssalts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl,flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleichydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methylazide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid,oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflamand tridiphane.

Preferred herbicides B that can be used in combination with thecompounds of the formula (I) according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl,diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl,haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop,quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim,tralkoxydim,4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-72-6);4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-45-3);4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione(CAS 1312340-84-3);5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312337-48-6);5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312340-82-1);5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1033760-55-2);4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1);4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); benfuresate,dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb,prosulfocarb, thiobencarb and triallate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium,chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron,diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron,florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam,flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl,imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium,iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron,metosulam, metsulfuron-methyl, nicosulfuron, orthosulfamuron,oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium,propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim,pyrimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium,pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron,thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron,tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl,tritosulfuron and triafamone;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxyniland its salts and esters, chloridazone, chlorotoluron, cyanazine,desmedipham, diquat-dibromide, diuron, fluometuron, hexazinone, ioxyniland its salts and esters, isoproturon, lenacil, linuron, metamitron,methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride,phenmedipham, propanil, pyridate, simazine, terbutryn, terbuthylazineand thidiazuron;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil,carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl,flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl,oxadiazon, oxyfluorfen, pentoxazone, pyraflufen-ethyl, saflufenacil,sulfentrazone, tiafenacil, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6; S-3100),N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452098-92-9),N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 915396-43-9),N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452099-05-7),N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide(CAS 452100-03-7),3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione(CAS 1258836-72-4),2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione;1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione,and3-[7-Chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione(CAS 212754-02-4);

b5) from the group of the bleacher herbicides:

aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone,clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone,flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen,pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione,topramezone and4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium, glyphosate-potassium andglyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

glufosinate, glufosinate-P, glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors: asulam;

b9) from the group of the mitosis inhibitors:

benfluralin, dithiopyr, ethalfluralin, oryzalin, pendimethalin,thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethenamid,dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor,metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M,pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlorand isoxazoline-compounds of the formulae II.1, II.2, II.3, II.4, II.5,II.6, II.7, II.8 and II.9 as mentioned above;

b11) from the group of the cellulose biosynthesis inhibitors:dichlobenil, flupoxam, isoxaben and1-Cyclohexyl-5-pentafluorphenyloxy-14-[1,2,4,6]thiatriazin-3-ylamine;

b13) from the group of the auxinic herbicides:

2,4-D and its salts and esters, aminocyclopyrachlor and its salts andesters, aminopyralid and its salts such asaminopyralid-dimethylammonium,aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, clopyralidand its salts and esters, dicamba and its salts and esters,dichlorprop-P and its salts and esters, fluroxypyr-meptyl, halauxifenand its salts and esters (CAS 943832-60-8), MCPA and its salts andesters, MCPB and its salts and esters, mecoprop-P and its salts andesters, picloram and its salts and esters, quinclorac, quinmerac andtriclopyr and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr anddiflufenzopyr-sodium;

b15) from the group of the other herbicides: bromobutide, cinmethylin,cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters,dalapon, difenzoquat, difenzoquat-metilsulfate, DSMA, dymron(=daimuron), flamprop, flamprop-isopropyl, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, indanofan, indaziflam, metam,methylbromide, MSMA, oxaziclomefone, pyributicarb, triaziflam andtridiphane.

Particularly preferred herbicides B that can be used in combination withthe compounds A of the formula (I) according to the present inventionare:

b1) from the group of the lipid biosynthesis inhibitors:clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl,pinoxaden, profoxydim, tepraloxydim, tralkoxydim,4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-72-6);4-(2′,4′-Dichloro-4-cyclopropyl[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1312337-45-3);4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one(CAS 1033757-93-5);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione(CAS 1312340-84-3);5-(Acetyloxy)-4-(4′-chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312337-48-6);5-(Acetyloxy)-4-(2′,4′-dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one;5-(Acetyloxy)-4-(4′-chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1312340-82-1);5-(Acetyloxy)-4-(2′,4′-dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one(CAS 1033760-55-2);4-(4′-Chloro-4-cyclopropyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312337-51-1);4-(2′,4′-Dichloro-4-cyclopropyl-[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester;4-(4′-Chloro-4-ethyl-2′-fluoro[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1312340-83-2);4-(2′,4′-Dichloro-4-ethyl[1,1′-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-ylcarbonic acid methyl ester (CAS 1033760-58-5); esprocarb, prosulfocarb,thiobencarb and triallate;

b2) from the group of the ALS inhibitors: bensulfuron-methyl,bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam,flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic,imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron,iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium,mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam,propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl,pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl,tritosulfuron and triafamone;

b3) from the group of the photosynthesis inhibitors: ametryn, atrazine,diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin,paraquat, paraquat-dichloride, propanil, terbutryn and terbuthylazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:flumioxazin, oxyfluorfen, saflufenacil, sulfentrazone, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate(CAS 353292-31-6)3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione,1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione(CAS 1258836-72-4),2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione,and1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides: amitrole, bicyclopyrone,clomazone, diflufenican, fenquintrione, flumeturon, flurochloridone,isoxaflutole, mesotrione, picolinafen, sulcotrione, tefuryltrione,tembotrione and topramezone;

b6) from the group of the EPSP synthase inhibitors: glyphosate,glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors: glufosinate,glufosinate-P and glufosinate-ammonium;

b9) from the group of the mitosis inhibitors: pendimethalin andtrifluralin;

b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole,dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor,metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone andpyroxasulfone; likewise, preference is given to isoxazoline compounds ofthe formulae II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 asmentioned above;

b11) from the group of the cellulose biosynthesis inhibitors: isoxaben;

b13) from the group of the auxinic herbicides: 2,4-D and its salts andesters such as clacyfos, and aminocyclopyrachlor and its salts andesters, aminopyralid and its salts and its esters, clopyralid and itssalts and esters, dicamba and its salts and esters, fluroxypyr-meptyl,quinclorac and quinmerac;

b14) from the group of the auxin transport inhibitors: diflufenzopyr anddiflufenzopyr-sodium,

b15) from the group of the other herbicides: dymron (=daimuron),indanofan, indaziflam, oxaziclomefone and triaziflam.

Active compounds B and C having a carboxyl group can be employed in theform of the acid, in the form of an agriculturally suitable salt asmentioned above or else in the form of an agriculturally acceptablederivative in the compositions according to the invention.

In the case of dicamba, suitable salts include those, where thecounterion is an agriculturally acceptable cation. For example, suitablesalts of dicamba are dicamba-sodium, dicamba-potassium,dicamba-methylammonium, dicamba-dimethylammonium,dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine,dicamba-diolamine, dicamba-trolamine,dicamba-N,N-bis-(3-aminopropyl)methylamine anddicamba-diethylenetriamine. Examples of a suitable ester aredicamba-methyl and dicamba-butotyl.

Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium,2,4-D-diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine),2,4-D-triethanolammonium, 2,4-D-isopropylammonium,2,4-D-triisopropanolammonium, 2,4-D-heptylammonium,2,4-D-dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium,2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium. Examples of suitableesters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl,2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl,2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl,2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl andclacyfos.

Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassiumand 2,4-DB-dimethylammonium. Suitable esters of 2,4-DB are for example2,4-DB-butyl and 2,4-DB-isoctyl.

Suitable salts of dichlorprop are for example dichlorprop-sodium,dichlorprop-potassium and dichlorprop-dimethylammonium. Examples ofsuitable esters of dichlorprop are dichlorprop-butotyl anddichlorprop-isoctyl.

Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl,MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl,MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium,MCPA-sodium and MCPA-trolamine.

A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB isMCPB-ethyl.

Suitable salts of clopyralid are clopyralid-potassium,clopyralid-olamine and clopyralid-tris-(2-hydroxypropyl)ammonium.Example of suitable esters of clopyralid is clopyralid-methyl.

Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl andfluroxypyr-2-butoxy-1-methylethyl, wherein fluroxypyr-meptyl ispreferred.

Suitable salts of picloram are picloram-dimethylammonium,picloram-potassium, picloram-triisopropanolammonium,picloram-triisopropylammonium and picloram-trolamine. A suitable esterof picloram is picloram-isoctyl.

A suitable salt of triclopyr is triclopyr-triethylammonium. Suitableesters of triclopyr are for example triclopyr-ethyl andtriclopyr-butotyl.

Suitable salts and esters of chloramben include chloramben-ammonium,chloramben-diolamine chloramben-methyl, chloramben-methylammonium andchloramben-sodium. Suitable salts and esters of 2,3,6-TBA include2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium and2,3,6-TBA-sodium.

Suitable salts and esters of aminopyralid includeaminopyralid-potassium, aminopyralid-dimethylammonium, andaminopyralid-tris(2-hydroxypropyl)ammonium.

Suitable salts of glyphosate are for example glyphosate-ammonium,glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium,glyphosate-trimesium as well as the ethanolamine and diethanolaminesalts, preferably glyphosate-diammonium, glyphosate-isopropylammoniumand glyphosate-trimesium (sulfosate).

A suitable salt of glufosinate is for example glufosinate-ammonium.

A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.

Suitable salts and esters of bromoxynil are for examplebromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate,bromoxynil-potassium and bromoxynil-sodium.

Suitable salts and esters of ioxonil are for example ioxonil-octanoate,ioxonil-potassium and ioxonil-sodium.

Suitable salts and esters of mecoprop include mecoprop-butotyl,mecoprop-dimethylammonium mecoprop-diolamine, mecoprop-ethadyl,mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl,mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.

Suitable salts of mecoprop-P are for example mecoprop-P-butotyl,mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl,mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.

A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.

A suitable salt of naptalam is for example naptalam-sodium.

Suitable salts and esters of aminocyclopyrachlor are for exampleaminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-methyl,aminocyclopyrachlor-triisopropanolammonium, aminocyclopyrachlor-sodiumand aminocyclopyrachlor-potassium.

A suitable salt of quinclorac is for examplequinclorac-dimethylammonium.

A suitable salt of quinmerac is for example quinclorac-dimethylammonium.

A suitable salt of imazamox is for example imazamox-ammonium.

Suitable salts of imazapic are for example imazapic-ammonium andimazapic-isopropylammonium.

Suitable salts of imazapyr are for example imazapyr-ammonium andimazapyr-isopropylammonium.

A suitable salt of imazaquin is for example imazaquin-ammonium.

Suitable salts of imazethapyr are for example imazethapyr-ammonium andimazethapyr-isopropylammonium.

A suitable salt of topramezone is for example topramezone-sodium.

Particularly preferred herbicidal compounds B are the herbicides B asdefined above; in particular the herbicides B.1-B.201 listed below intable B:

TABLE B Herbicide B B.1 clethodim B.2 clodinafop-propargyl B.3cycloxydim B.4 cyhalofop-butyl B.5 fenoxaprop-ethyl B.6fenoxaprop-P-ethyl B.7 metamifop B.8 pinoxaden B.9 profoxydim B.10sethoxydim B.11 tepraloxydim B.12 tralkoxydim B.13 esprocarb B.14ethofumesate B.15 molinate B.16 prosulfocarb B.17 thiobencarb B.18triallate B.19 bensulfuron-methyl B.20 bispyribac-sodium B.21cloransulam-methyl B.22 chlorsulfuron B.23 clorimuron B.24cyclosulfamuron B.25 diclosulam B.26 florasulam B.27 flumetsulam B.28flupyrsulfuron-methyl-sodium B.29 foramsulfuron B.30 imazamox B.31imazamox-ammonium B.32 imazapic B.33 imazapic-ammonium B.34imazapic-isopropylammonium B.35 imazapyr B.36 imazapyr-ammonium B.37imazapyr-isopropylammonium B.38 imazaquin B.39 imazaquin-ammonium B.40imazethapyr B.41 imazethapyr-ammonium B.42 imazethapyr-isopropylammoniumB.43 imazosulfuron B.44 iodosulfuron-methyl-sodium B.45 iofensulfuronB.46 iofensulfuron-sodium B.47 mesosulfuron-methyl B.48 metazosulfuronB.49 metsulfuron-methyl B.50 metosulam B.51 nicosulfuron B.52 penoxsulamB.53 propoxycarbazon-sodium B.54 pyrazosulfuron-ethyl B.55 pyribenzoximB.56 pyriftalid B.57 pyroxsulam B.58 propyrisulfuron B.59 rimsulfuronB.60 sulfosulfuron B.61 thiencarbazone-methyl B.62 thifensulfuron-methylB.63 tribenuron-methyl B.64 tritosulfuron B.65 triafamone B.66 ametryneB.67 atrazine B.68 bentazon B.69 bromoxynil B.70 bromoxynil-octanoateB.71 bromoxynil-heptanoate B.72 bromoxynil-potassium B.73 diuron B.74fluometuron B.75 hexazinone B.76 isoproturon B.77 linuron B.78metamitron B.79 metribuzin B.80 propanil B.81 simazin B.82terbuthylazine B.83 terbutryn B.84 paraquat-dichloride B.85 acifluorfenB.86 butafenacil B.87 carfentrazone-ethyl B.88 flumioxazin B.89fomesafen B.90 oxadiargyl B.91 oxyfluorfen B.92 pyraflufen B.93pyraflufen-ethyl B.94 saflufenacil B.95 sulfentrazone B.96trifludimoxazin B.97 ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2- pyridyloxy]acetate(CAS 353292-31-6) B.98 benzobicyclon B.99 bicyclopyrone B.100 clomazoneB.101 diflufenican B.102 flurochloridone B.103 isoxaflutole B.104mesotrione B.105 norflurazone B.106 picolinafen B.107 sulcotrione B.108tefuryltrione B.109 tembotrione B.110 tolpyralate B.111 topramezoneB.112 topramezone-sodium B.113 amitrole B.114 fluometuron B.115fenquinotrione B.116 glyphosate B.117 glyphosate-ammonium B.118glyphosate-dimethylammonium B.119 glyphosate-isopropylammonium B.120glyphosate-trimesium (sulfosate) B.121 glyphosate-potassium B.122glufosinate B.123 glufosinate-ammonium B.124 glufosinate-P B.125glufosinate-P-ammonium B.126 pendimethalin B.127 trifluralin B.128acetochlor B.129 butachlor B.130 cafenstrole B.131 dimethenamid-P B.132fentrazamide B.133 flufenacet B.134 mefenacet B.135 metazachlor B.136metolachlor B.137 S-metolachlor B.138 pretilachlor B.139 fenoxasulfoneB.140 indaziflam B.141 isoxaben B.142 triaziflam B.143 ipfencarbazoneB.144 pyroxasulfone B.145 2,4-D B.146 2,4-D-isobutyl B.1472,4-D-dimethylammonium B.148 2,4-D-N,N,N-trimethylethanolammonium B.149aminopyralid B.150 aminopyralid-methyl B.151aminopyralid-dimethyl-ammonium B.152aminopyralid-tris(2-hydroxypropyl)ammonium B.153 clopyralid B.154clopyralid-methyl B.155 clopyralid-olamine B.156 dicamba B.157dicamba-butotyl B.158 dicamba-diglycolamine B.159dicamba-dimethylammonium B.160 dicamba-diolamine B.161dicamba-isopropylammonium B.162 dicamba-potassium B.163 dicamba-sodiumB.164 dicamba-trolamine B.165 dicamba-N,N-bis-(3-aminopropyl)methylamineB.166 dicamba-diethylenetriamine B.167 fluroxypyr B.168fluroxypyr-meptyl B.169 halauxifen B.170 halauxifen-methyl B.171 MCPAB.172 MCPA-2-ethylhexyl B.173 MCPA-dimethylammonium B.174 quincloracB.175 quinclorac-dimethylammonium B.176 quinmerac B.177quinmerac-dimethylammonium B.178 florpyrauxifen B.179florpyrauxifen-benzyl (CAS 1390661-72-9) B.180 aminocyclopyrachlor B.181aminocyclopyrachlor-potassium B.182 aminocyclopyrachlor-methyl B.183diflufenzopyr B.184 diflufenzopyr-sodium B.185 dymron B.186 indanofanB.187 oxaziclomefone B.188 II.1 B.189 II.2 B.190 II.3 B.191 II.4 B.192II.5 B.193 II.6 B.194 II.7 B.195 II.8 B.196 II.9 B.1974-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS1629965-65-6) B.198 flopyrauxifen B.199 oxotrione (CAS 1486617-21-3)B.200 cinmethylin B.2012-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0)

Moreover, it may be useful to apply the compounds of formula (I) incombination with safeners and optionally with one or more furtherheribicides. Safeners are chemical compounds which prevent or reducedamage on useful plants without having a major impact on the herbicidalaction of the compounds of the formula (I) towards unwanted plants. Theycan be applied either before sowings (e.g. on seed treatments, shoots orseedlings) or in the pre-emergence application or post-emergenceapplication of the useful plant. The safeners and the compounds offormula (I) and optionally the herbicides B can be appliedsimultaneously or in succession.

Suitable safeners are e.g. (quinolin-8-oxy)acetic acids,1-phenyl-5-haloalkyl-1H-1,2,4-triazol-3-carboxylic acids,1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazol-3,5-dicarboxylic acids,4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides,alpha-oximinophenylacetonitriles, acetophenonoximes,4,6-dihalo-2-phenylpyrimidines,N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1,8-naphthalicanhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids,phosphorthiolates and N-alkyl-O-phenylcarbamates and theiragriculturally acceptable salts and their agriculturally acceptablederivatives such amides, esters, and thioesters, provided they have anacid group.

Examples of preferred safeners C are benoxacor, cloquintocet,cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate,fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen,mefenpyr, mephenate, naphthalic anhydride, oxabetrinil,4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine(R-29148, CAS 52836-31-4) andN-(2-Methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide(CAS 129531-12-0).

Particularly preferred safeners C are the following compounds C.1 toC.17 listed in table C.

TABLE C C.1 benoxacor C.2 cloquintocet C.3 cloquintocet-mexyl C.4cyprosulfamide C.5 dichlormid C.6 fenchlorazole C.7 fenchlorazole-ethylC.8 fenclorim C.9 furilazole C.10 isoxadifen C.11 isoxadifen-ethyl C.12mefenpyr C.13 mefenpyr-diethyl C.14 naphtalic acid anhydride C.154-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane C.162,2,5-trimethyl-3-(dichloroacetyl)- 1,3-oxazolidine C.17N-(2-Methoxybenzoyl)-4- [(methylaminocarbonyl)amino]benzenesulfonamide

The active compounds B of groups b1) to b15) and the safener compounds Care known herbicides and safeners, see, for example, The Compendium ofPesticide Common Names (http://www.alanwood.net/pesticides/); FarmChemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B.Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg ThiemeVerlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition,Weed Science Society of America, 1994; and K. K. Hatzios, HerbicideHandbook, Supplement for the 7th edition, Weed Science Society ofAmerica, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine [CASNo. 52836-31-4] is also referred to as R-29148.4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] isalso referred to as AD-67 and MON 4660.

The assignment of the active compounds to the respective mechanisms ofaction is based on current knowledge. If several mechanisms of actionapply to one active compound, this substance was only assigned to onemechanism of action.

The weight ratios of the individual components in the preferred mixturesmentioned below are within the limits given above, in particular withinthe preferred limits.

Particularly preferred are the compositions mentioned below comprisingthe compound of the formula I as defined above and the substance(s) asdefined in the respective row of table 1;

especially preferred comprising as only herbicidal active compoundscompounds I.a.A-1.1-I.a.A-1.192, I.b.A-2.1-I.b.A-2.192,I.c.A-3.1-I.c.A-3.192 as defined and the substance(s) as defined in therespective row of table 1;

TABLE 1 comp. herbicide safener no. B C 1.1 B.1 — 1.2 B.2 — 1.3 B.3 —1.4 B.4 — 1.5 B.5 — 1.6 B.6 — 1.7 B.7 — 1.8 B.8 — 1.9 B.9 — 1.10 B.10 —1.11 B.11 — 1.12 B.12 — 1.13 B.13 — 1.14 B.14 — 1.15 B.15 — 1.16 B.16 —1.17 B.17 — 1.18 B.18 — 1.19 B.19 — 1.20 B.20 — 1.21 B.21 — 1.22 B.22 —1.23 B.23 — 1.24 B.24 — 1.25 B.25 — 1.26 B.26 — 1.27 B.27 — 1.28 B.28 —1.29 B.29 — 1.30 B.30 — 1.31 B.31 — 1.32 B.32 — 1.33 B.33 — 1.34 B.34 —1.35 B.35 — 1.36 B.36 — 1.37 B.37 — 1.38 B.38 — 1.39 B.39 — 1.40 B.40 —1.41 B.41 — 1.42 B.42 — 1.43 B.43 — 1.44 B.44 — 1.45 B.45 — 1.46 B.46 —1.47 B.47 — 1.48 B.48 — 1.49 B.49 — 1.50 B.50 — 1.51 B.51 — 1.52 B.52 —1.53 B.53 — 1.54 B.54 — 1.55 B.55 — 1.56 B.56 — 1.57 B.57 — 1.58 B.58. —1.59 B.59 — 1.60 B.60 — 1.61 B.61 — 1.62 B.62 — 1.63 B.63 — 1.64 B.64 —1.65 B.65 — 1.66 B.66 — 1.67 B.67 — 1.68 B.68 — 1.69 B.69 — 1.70 B.70 —1.71 B.71 — 1.72 B.72 — 1.73 B.73 — 1.74 B.74 — 1.75 B.75 — 1.76 B.76 —1.77 B.77 — 1.78 B.78 — 1.79 B.79 — 1.80 B.80 — 1.81 B.81 — 1.82 B.82 —1.83 B.83 — 1.84 B.84 — 1.85 B.85 — 1.86 B.86 — 1.87 B.87 — 1.88 B.88 —1.89 B.89 — 1.90 B.90 — 1.91 B.91 — 1.92 B.92 — 1.93 B.93 — 1.94 B.94 —1.95 B.95 — 1.96 B.96 — 1.97 B.97 — 1.98 B.98 — 1.99 B.99 — 1.100 B.100— 1.101 B.101 — 1.102 B.102 — 1.103 B.103 — 1.104 B.104 — 1.105 B.105 —1.106 B.106 — 1.107 B.107 — 1.108 B.108 — 1.109 B.109 — 1.110 B.110 —1.111 B.111 — 1.112 B.112 — 1.113 B.113 — 1.114 B.114 — 1.115 B.115 —1.116 B.116 — 1.117 B.117 — 1.118 B.118 — 1.119 B.119 — 1.120 B.120 —1.121 B.121 — 1.122 B.122 — 1.123 B.123 — 1.124 B.124 — 1.125 B.125 —1.126 B.126 — 1.127 B.127 — 1.128 B.128 — 1.129 B.129 — 1.130 B.130 —1.131 B.131 — 1.132 B.132 — 1.133 B.133 — 1.134 B.134 — 1.135 B.135 —1.136 B.136 — 1.137 B.137 — 1.138 B.138 — 1.139 B.139 — 1.140 B.140 —1.141 B.141 — 1.142 B.142 — 1.143 B.143 — 1.144 B.144 — 1.145 B.145 —1.146 B.146 — 1.147 B.147 — 1.148 B.148 — 1.149 B.149 — 1.150 B.150 —1.151 B.151 — 1.152 B.152 — 1.153 B.153 — 1.154 B.154 — 1.155 B.155 —1.156 B.156 — 1.157 B.157 — 1.158 B.158 — 1.159 B.159 — 1.160 B.160 —1.161 B.161 — 1.162 B.162 — 1.163 B.163 — 1.164 B.164 — 1.165 B.165 —1.166 B.166 — 1.167 B.167 — 1.168 B.168 — 1.169 B.169 — 1.170 B.170 —1.171 B.171 — 1.172 B.172 — 1.173 B.173 — 1.174 B.174 — 1.175 B.175 —1.176 B.176 — 1.177 B.177 — 1.178 B.178 — 1.179 B.179 — 1.180 B.180 —1.181 B.181 — 1.182 B.182 — 1.183 B.183 — 1.184 B.184 — 1.185 B.185 —1.186 B.186 — 1.187 B.187 — 1.188 B.188 — 1.189 B.189 — 1.190 B.190 —1.191 B.191 — 1.192 B.192 — 1.193 B.193 — 1.194 B.194 — 1.195 B.195 —1.196 B.196 — 1.197 B.197 — 1.198 B.198 — 1.199 B.199 — 1.200 B.200 —1.201 B.201 — 1.202 B.1 C.1 1.203 B.2 C.1 1.204 B.3 C.1 1.205 B.4 C.11.206 B.5 C.1 1.207 B.6 C.1 1.208 B.7 C.1 1.209 B.8 C.1 1.210 B.9 C.11.211 B.10 C.1 1.212 B.11 C.1 1.213 B.12 C.1 1.214 B.13 C.1 1.215 B.14C.1 1.216 B.15 C.1 1.217 B.16 C.1 1.218 B.17 C.1 1.219 B.18 C.1 1.220B.19 C.1 1.221 B.20 C.1 1.222 B.21 C.1 1.223 B.22 C.1 1.224 B.23 C.11.225 B.24 C.1 1.226 B.25 C.1 1.227 B.26 C.1 1.228 B.27 C.1 1.229 B.28C.1 1.230 B.29 C.1 1.231 B.30 C.1 1.232 B.31 C.1 1.233 B.32 C.1 1.234B.33 C.1 1.235 B.34 C.1 1.236 B.35 C.1 1.237 B.36 C.1 1.238 B.37 C.11.239 B.38 C.1 1.240 B.39 C.1 1.241 B.40 C.1 1.242 B.41 C.1 1.243 B.42C.1 1.244 B.43 C.1 1.245 B.44 C.1 1.246 B.45 C.1 1.247 B.46 C.1 1.248B.47 C.1 1.249 B.48 C.1 1.250 B.49 C.1 1.251 B.50 C.1 1.252 B.51 C.11.253 B.52 C.1 1.254 B.53 C.1 1.255 B.54 C.1 1.256 B.55 C.1 1.257 B.56C.1 1.258 B.57 C.1 1.259 B.58. C.1 1.260 B.59 C.1 1.261 B.60 C.1 1.262B.61 C.1 1.263 B.62 C.1 1.264 B.63 C.1 1.265 B.64 C.1 1.266 B.65 C.11.267 B.66 C.1 1.268 B.67 C.1 1.269 B.68 C.1 1.270 B.69 C.1 1.271 B.70C.1 1.272 B.71 C.1 1.273 B.72 C.1 1.274 B.73 C.1 1.275 B.74 C.1 1.276B.75 C.1 1.277 B.76 C.1 1.278 B.77 C.1 1.279 B.78 C.1 1.280 B.79 C.11.281 B.80 C.1 1.282 B.81 C.1 1.283 B.82 C.1 1.284 B.83 C.1 1.285 B.84C.1 1.286 B.85 C.1 1.287 B.86 C.1 1.288 B.87 C.1 1.289 B.88 C.1 1.290B.89 C.1 1.291 B.90 C.1 1.292 B.91 C.1 1.293 B.92 C.1 1.294 B.93 C.11.295 B.94 C.1 1.296 B.95 C.1 1.297 B.96 C.1 1.298 B.97 C.1 1.299 B.98C.1 1.300 B.99 C.1 1.301 B.100 C.1 1.302 B.101 C.1 1.303 B.102 C.1 1.304B.103 C.1 1.305 B.104 C.1 1.306 B.105 C.1 1.307 B.106 C.1 1.308 B.107C.1 1.309 B.108 C.1 1.310 B.109 C.1 1.311 B.110 C.1 1.312 B.111 C.11.313 B.112 C.1 1.314 B.113 C.1 1.315 B.114 C.1 1.316 B.115 C.1 1.317B.116 C.1 1.318 B.117 C.1 1.319 B.118 C.1 1.320 B.119 C.1 1.321 B.120C.1 1.322 B.121 C.1 1.323 B.122 C.1 1.324 B.123 C.1 1.325 B.124 C.11.326 B.125 C.1 1.327 B.126 C.1 1.328 B.127 C.1 1.329 B.128 C.1 1.330B.129 C.1 1.331 B.130 C.1 1.332 B.131 C.1 1.333 B.132 C.1 1.334 B.133C.1 1.335 B.134 C.1 1.336 B.135 C.1 1.337 B.136 C.1 1.338 B.137 C.11.339 B.138 C.1 1.340 B.139 C.1 1.341 B.140 C.1 1.342 B.141 C.1 1.343B.142 C.1 1.344 B.143 C.1 1.345 B.144 C.1 1.346 B.145 C.1 1.347 B.146C.1 1.348 B.147 C.1 1.349 B.148 C.1 1.350 B.149 C.1 1.351 B.150 C.11.352 B.151 C.1 1.353 B.152 C.1 1.354 B.153 C.1 1.355 B.154 C.1 1.356B.155 C.1 1.357 B.156 C.1 1.358 B.157 C.1 1.359 B.158 C.1 1.360 B.159C.1 1.361 B.160 C.1 1.362 B.161 C.1 1.363 B.162 C.1 1.364 B.163 C.11.365 B.164 C.1 1.366 B.165 C.1 1.367 B.166 C.1 1.368 B.167 C.1 1.369B.168 C.1 1.370 B.169 C.1 1.371 B.170 C.1 1.372 B.171 C.1 1.373 B.172C.1 1.374 B.173 C.1 1.375 B.174 C.1 1.376 B.175 C.1 1.377 B.176 C.11.378 B.177 C.1 1.379 B.178 C.1 1.380 B.179 C.1 1.381 B.180 C.1 1.382B.181 C.1 1.383 B.182 C.1 1.384 B.183 C.1 1.385 B.184 C.1 1.386 B.185C.1 1.387 B.186 C.1 1.388 B.187 C.1 1.389 B.188 C.1 1.390 B.189 C.11.391 B.190 C.1 1.392 B.191 C.1 1.393 B.192 C.1 1.394 B.193 C.1 1.395B.194 C.1 1.396 B.195 C.1 1.397 B.196 C.1 1.398 B.197 C.1 1.399 B.198C.1 1.400 B.199 C.1 1.401 B.200 C.1 1.402 B.201 C.1 1.403 B.1 C.2 1.404B.2 C.2 1.405 B.3 C.2 1.406 B.4 C.2 1.407 B.5 C.2 1.408 B.6 C.2 1.409B.7 C.2 1.410 B.8 C.2 1.411 B.9 C.2 1.412 B.10 C.2 1.413 B.11 C.2 1.414B.12 C.2 1.415 B.13 C.2 1.416 B.14 C.2 1.417 B.15 C.2 1.418 B.16 C.21.419 B.17 C.2 1.420 B.18 C.2 1.421 B.19 C.2 1.422 B.20 C.2 1.423 B.21C.2 1.424 B.22 C.2 1.425 B.23 C.2 1.426 B.24 C.2 1.427 B.25 C.2 1.428B.26 C.2 1.429 B.27 C.2 1.430 B.28 C.2 1.431 B.29 C.2 1.432 B.30 C.21.433 B.31 C.2 1.434 B.32 C.2 1.435 B.33 C.2 1.436 B.34 C.2 1.437 B.35C.2 1.438 B.36 C.2 1.439 B.37 C.2 1.440 B.38 C.2 1.441 B.39 C.2 1.442B.40 C.2 1.443 B.41 C.2 1.444 B.42 C.2 1.445 B.43 C.2 1.446 B.44 C.21.447 B.45 C.2 1.448 B.46 C.2 1.449 B.47 C.2 1.450 B.48 C.2 1.451 B.49C.2 1.452 B.50 C.2 1.453 B.51 C.2 1.454 B.52 C.2 1.455 B.53 C.2 1.456B.54 C.2 1.457 B.55 C.2 1.458 B.56 C.2 1.459 B.57 C.2 1.460 B.58. C.21.461 B.59 C.2 1.462 B.60 C.2 1.463 B.61 C.2 1.464 B.62 C.2 1.465 B.63C.2 1.466 B.64 C.2 1.467 B.65 C.2 1.468 B.66 C.2 1.469 B.67 C.2 1.470B.68 C.2 1.471 B.69 C.2 1.472 B.70 C.2 1.473 B.71 C.2 1.474 B.72 C.21.475 B.73 C.2 1.476 B.74 C.2 1.477 B.75 C.2 1.478 B.76 C.2 1.479 B.77C.2 1.480 B.78 C.2 1.481 B.79 C.2 1.482 B.80 C.2 1.483 B.81 C.2 1.484B.82 C.2 1.485 B.83 C.2 1.486 B.84 C.2 1.487 B.85 C.2 1.488 B.86 C.21.489 B.87 C.2 1.490 B.88 C.2 1.491 B.89 C.2 1.492 B.90 C.2 1.493 B.91C.2 1.494 B.92 C.2 1.495 B.93 C.2 1.496 B.94 C.2 1.497 B.95 C.2 1.498B.96 C.2 1.499 B.97 C.2 1.500 B.98 C.2 1.501 B.99 C.2 1.502 B.100 C.21.503 B.101 C.2 1.504 B.102 C.2 1.505 B.103 C.2 1.506 B.104 C.2 1.507B.105 C.2 1.508 B.106 C.2 1.509 B.107 C.2 1.510 B.108 C.2 1.511 B.109C.2 1.512 B.110 C.2 1.513 B.111 C.2 1.514 B.112 C.2 1.515 B.113 C.21.516 B.114 C.2 1.517 B.115 C.2 1.518 B.116 C.2 1.519 B.117 C.2 1.520B.118 C.2 1.521 B.119 C.2 1.522 B.120 C.2 1.523 B.121 C.2 1.524 B.122C.2 1.525 B.123 C.2 1.526 B.124 C.2 1.527 B.125 C.2 1.528 B.126 C.21.529 B.127 C.2 1.530 B.128 C.2 1.531 B.129 C.2 1.532 B.130 C.2 1.533B.131 C.2 1.534 B.132 C.2 1.535 B.133 C.2 1.536 B.134 C.2 1.537 B.135C.2 1.538 B.136 C.2 1.539 B.137 C.2 1.540 B.138 C.2 1.541 B.139 C.21.542 B.140 C.2 1.543 B.141 C.2 1.544 B.142 C.2 1.545 B.143 C.2 1.546B.144 C.2 1.547 B.145 C.2 1.548 B.146 C.2 1.549 B.147 C.2 1.550 B.148C.2 1.551 B.149 C.2 1.552 B.150 C.2 1.553 B.151 C.2 1.554 B.152 C.21.555 B.153 C.2 1.556 B.154 C.2 1.557 B.155 C.2 1.558 B.156 C.2 1.559B.157 C.2 1.560 B.158 C.2 1.561 B.159 C.2 1.562 B.160 C.2 1.563 B.161C.2 1.564 B.162 C.2 1.565 B.163 C.2 1.566 B.164 C.2 1.567 B.165 C.21.568 B.166 C.2 1.569 B.167 C.2 1.570 B.168 C.2 1.571 B.169 C.2 1.572B.170 C.2 1.573 B.171 C.2 1.574 B.172 C.2 1.575 B.173 C.2 1.576 B.174C.2 1.577 B.175 C.2 1.578 B.176 C.2 1.579 B.177 C.2 1.580 B.178 C.21.581 B.179 C.2 1.582 B.180 C.2 1.583 B.181 C.2 1.584 B.182 C.2 1.585B.183 C.2 1.586 B.184 C.2 1.587 B.185 C.2 1.588 B.186 C.2 1.589 B.187C.2 1.590 B.188 C.2 1.591 B.189 C.2 1.592 B.190 C.2 1.593 B.191 C.21.594 B.192 C.2 1.595 B.193 C.2 1.596 B.194 C.2 1.597 B.195 C.2 1.598B.196 C.2 1.599 B.197 C.2 1.600 B.198 C.2 1.601 B.199 C.2 1.602 B.200C.2 1.603 B.201 C.2 1.604 B.1 C.3 1.605 B.2 C.3 1.606 B.3 C.3 1.607 B.4C.3 1.608 B.5 C.3 1.609 B.6 C.3 1.610 B.7 C.3 1.611 B.8 C.3 1.612 B.9C.3 1.613 B.10 C.3 1.614 B.11 C.3 1.615 B.12 C.3 1.616 B.13 C.3 1.617B.14 C.3 1.618 B.15 C.3 1.619 B.16 C.3 1.620 B.17 C.3 1.621 B.18 C.31.622 B.19 C.3 1.623 B.20 C.3 1.624 B.21 C.3 1.625 B.22 C.3 1.626 B.23C.3 1.627 B.24 C.3 1.628 B.25 C.3 1.629 B.26 C.3 1.630 B.27 C.3 1.631B.28 C.3 1.632 B.29 C.3 1.633 B.30 C.3 1.634 B.31 C.3 1.635 B.32 C.31.636 B.33 C.3 1.637 B.34 C.3 1.638 B.35 C.3 1.639 B.36 C.3 1.640 B.37C.3 1.641 B.38 C.3 1.642 B.39 C.3 1.643 B.40 C.3 1.644 B.41 C.3 1.645B.42 C.3 1.646 B.43 C.3 1.647 B.44 C.3 1.648 B.45 C.3 1.649 B.46 C.31.650 B.47 C.3 1.651 B.48 C.3 1.652 B.49 C.3 1.653 B.50 C.3 1.654 B.51C.3 1.655 B.52 C.3 1.656 B.53 C.3 1.657 B.54 C.3 1.658 B.55 C.3 1.659B.56 C.3 1.660 B.57 C.3 1.661 B.58. C.3 1.662 B.59 C.3 1.663 B.60 C.31.664 B.61 C.3 1.665 B.62 C.3 1.666 B.63 C.3 1.667 B.64 C.3 1.668 B.65C.3 1.669 B.66 C.3 1.670 B.67 C.3 1.671 B.68 C.3 1.672 B.69 C.3 1.673B.70 C.3 1.674 B.71 C.3 1.675 B.72 C.3 1.676 B.73 C.3 1.677 B.74 C.31.678 B.75 C.3 1.679 B.76 C.3 1.680 B.77 C.3 1.681 B.78 C.3 1.682 B.79C.3 1.683 B.80 C.3 1.684 B.81 C.3 1.685 B.82 C.3 1.686 B.83 C.3 1.687B.84 C.3 1.688 B.85 C.3 1.689 B.86 C.3 1.690 B.87 C.3 1.691 B.88 C.31.692 B.89 C.3 1.693 B.90 C.3 1.694 B.91 C.3 1.695 B.92 C.3 1.696 B.93C.3 1.697 B.94 C.3 1.698 B.95 C.3 1.699 B.96 C.3 1.700 B.97 C.3 1.701B.98 C.3 1.702 B.99 C.3 1.703 B.100 C.3 1.704 B.101 C.3 1.705 B.102 C.31.706 B.103 C.3 1.707 B.104 C.3 1.708 B.105 C.3 1.709 B.106 C.3 1.710B.107 C.3 1.711 B.108 C.3 1.712 B.109 C.3 1.713 B.110 C.3 1.714 B.111C.3 1.715 B.112 C.3 1.716 B.113 C.3 1.717 B.114 C.3 1.718 B.115 C.31.719 B.116 C.3 1.720 B.117 C.3 1.721 B.118 C.3 1.722 B.119 C.3 1.723B.120 C.3 1.724 B.121 C.3 1.725 B.122 C.3 1.726 B.123 C.3 1.727 B.124C.3 1.728 B.125 C.3 1.729 B.126 C.3 1.730 B.127 C.3 1.731 B.128 C.31.732 B.129 C.3 1.733 B.130 C.3 1.734 B.131 C.3 1.735 B.132 C.3 1.736B.133 C.3 1.737 B.134 C.3 1.738 B.135 C.3 1.739 B.136 C.3 1.740 B.137C.3 1.741 B.138 C.3 1.742 B.139 C.3 1.743 B.140 C.3 1.744 B.141 C.31.745 B.142 C.3 1.746 B.143 C.3 1.747 B.144 C.3 1.748 B.145 C.3 1.749B.146 C.3 1.750 B.147 C.3 1.751 B.148 C.3 1.752 B.149 C.3 1.753 B.150C.3 1.754 B.151 C.3 1.755 B.152 C.3 1.756 B.153 C.3 1.757 B.154 C.31.758 B.155 C.3 1.759 B.156 C.3 1.760 B.157 C.3 1.761 B.158 C.3 1.762B.159 C.3 1.763 B.160 C.3 1.764 B.161 C.3 1.765 B.162 C.3 1.766 B.163C.3 1.767 B.164 C.3 1.768 B.165 C.3 1.769 B.166 C.3 1.770 B.167 C.31.771 B.168 C.3 1.772 B.169 C.3 1.773 B.170 C.3 1.774 B.171 C.3 1.775B.172 C.3 1.776 B.173 C.3 1.777 B.174 C.3 1.778 B.175 C.3 1.779 B.176C.3 1.780 B.177 C.3 1.781 B.178 C.3 1.782 B.179 C.3 1.783 B.180 C.31.784 B.181 C.3 1.785 B.182 C.3 1.786 B.183 C.3 1.787 B.184 C.3 1.788B.185 C.3 1.789 B.186 C.3 1.790 B.187 C.3 1.791 B.188 C.3 1.792 B.189C.3 1.793 B.190 C.3 1.794 B.191 C.3 1.795 B.192 C.3 1.796 B.193 C.31.797 B.194 C.3 1.798 B.195 C.3 1.799 B.196 C.3 1.800 B.197 C.3 1.801B.198 C.3 1.802 B.199 C.3 1.803 B.200 C.3 1.804 B.201 C.3 1.805 B.1 C.41.806 B.2 C.4 1.807 B.3 C.4 1.808 B.4 C.4 1.809 B.5 C.4 1.810 B.6 C.41.811 B.7 C.4 1.812 B.8 C.4 1.813 B.9 C.4 1.814 B.10 C.4 1.815 B.11 C.41.816 B.12 C.4 1.817 B.13 C.4 1.818 B.14 C.4 1.819 B.15 C.4 1.820 B.16C.4 1.821 B.17 C.4 1.822 B.18 C.4 1.823 B.19 C.4 1.824 B.20 C.4 1.825B.21 C.4 1.826 B.22 C.4 1.827 B.23 C.4 1.828 B.24 C.4 1.829 B.25 C.41.830 B.26 C.4 1.831 B.27 C.4 1.832 B.28 C.4 1.833 B.29 C.4 1.834 B.30C.4 1.835 B.31 C.4 1.836 B.32 C.4 1.837 B.33 C.4 1.838 B.34 C.4 1.839B.35 C.4 1.840 B.36 C.4 1.841 B.37 C.4 1.842 B.38 C.4 1.843 B.39 C.41.844 B.40 C.4 1.845 B.41 C.4 1.846 B.42 C.4 1.847 B.43 C.4 1.848 B.44C.4 1.849 B.45 C.4 1.850 B.46 C.4 1.851 B.47 C.4 1.852 B.48 C.4 1.853B.49 C.4 1.854 B.50 C.4 1.855 B.51 C.4 1.856 B.52 C.4 1.857 B.53 C.41.858 B.54 C.4 1.859 B.55 C.4 1.860 B.56 C.4 1.861 B.57 C.4 1.862 B.58.C.4 1.863 B.59 C.4 1.864 B.60 C.4 1.865 B.61 C.4 1.866 B.62 C.4 1.867B.63 C.4 1.868 B.64 C.4 1.869 B.65 C.4 1.870 B.66 C.4 1.871 B.67 C.41.872 B.68 C.4 1.873 B.69 C.4 1.874 B.70 C.4 1.875 B.71 C.4 1.876 B.72C.4 1.877 B.73 C.4 1.878 B.74 C.4 1.879 B.75 C.4 1.880 B.76 C.4 1.881B.77 C.4 1.882 B.78 C.4 1.883 B.79 C.4 1.884 B.80 C.4 1.885 B.81 C.41.886 B.82 C.4 1.887 B.83 C.4 1.888 B.84 C.4 1.889 B.85 C.4 1.890 B.86C.4 1.891 B.87 C.4 1.892 B.88 C.4 1.893 B.89 C.4 1.894 B.90 C.4 1.895B.91 C.4 1.896 B.92 C.4 1.897 B.93 C.4 1.898 B.94 C.4 1.899 B.95 C.41.900 B.96 C.4 1.901 B.97 C.4 1.902 B.98 C.4 1.903 B.99 C.4 1.904 B.100C.4 1.905 B.101 C.4 1.906 B.102 C.4 1.907 B.103 C.4 1.908 B.104 C.41.909 B.105 C.4 1.910 B.106 C.4 1.911 B.107 C.4 1.912 B.108 C.4 1.913B.109 C.4 1.914 B.110 C.4 1.915 B.111 C.4 1.916 B.112 C.4 1.917 B.113C.4 1.918 B.114 C.4 1.919 B.115 C.4 1.920 B.116 C.4 1.921 B.117 C.41.922 B.118 C.4 1.923 B.119 C.4 1.924 B.120 C.4 1.925 B.121 C.4 1.926B.122 C.4 1.927 B.123 C.4 1.928 B.124 C.4 1.929 B.125 C.4 1.930 B.126C.4 1.931 B.127 C.4 1.932 B.128 C.4 1.933 B.129 C.4 1.934 B.130 C.41.935 B.131 C.4 1.936 B.132 C.4 1.937 B.133 C.4 1.938 B.134 C.4 1.939B.135 C.4 1.940 B.136 C.4 1.941 B.137 C.4 1.942 B.138 C.4 1.943 B.139C.4 1.944 B.140 C.4 1.945 B.141 C.4 1.946 B.142 C.4 1.947 B.143 C.41.948 B.144 C.4 1.949 B.145 C.4 1.950 B.146 C.4 1.951 B.147 C.4 1.952B.148 C.4 1.953 B.149 C.4 1.954 B.150 C.4 1.955 B.151 C.4 1.956 B.152C.4 1.957 B.153 C.4 1.958 B.154 C.4 1.959 B.155 C.4 1.960 B.156 C.41.961 B.157 C.4 1.962 B.158 C.4 1.963 B.159 C.4 1.964 B.160 C.4 1.965B.161 C.4 1.966 B.162 C.4 1.967 B.163 C.4 1.968 B.164 C.4 1.969 B.165C.4 1.970 B.166 C.4 1.971 B.167 C.4 1.972 B.168 C.4 1.973 B.169 C.41.974 B.170 C.4 1.975 B.171 C.4 1.976 B.172 C.4 1.977 B.173 C.4 1.978B.174 C.4 1.979 B.175 C.4 1.980 B.176 C.4 1.981 B.177 C.4 1.982 B.178C.4 1.983 B.179 C.4 1.984 B.180 C.4 1.985 B.181 C.4 1.986 B.182 C.41.987 B.183 C.4 1.988 B.184 C.4 1.989 B.185 C.4 1.990 B.186 C.4 1.991B.187 C.4 1.992 B.188 C.4 1.993 B.189 C.4 1.994 B.190 C.4 1.995 B.191C.4 1.996 B.192 C.4 1.997 B.193 C.4 1.998 B.194 C.4 1.999 B.195 C.41.1000 B.196 C.4 1.1001 B.197 C.4 1.1002 B.198 C.4 1.1003 B.199 C.41.1004 B.200 C.4 1.1005 B.201 C.4 1.1006 B.1 C.5 1.1007 B.2 C.5 1.1008B.3 C.5 1.1009 B.4 C.5 1.1010 B.5 C.5 1.1011 B.6 C.5 1.1012 B.7 C.51.1013 B.8 C.5 1.1014 B.9 C.5 1.1015 B.10 C.5 1.1016 B.11 C.5 1.1017B.12 C.5 1.1018 B.13 C.5 1.1019 B.14 C.5 1.1020 B.15 C.5 1.1021 B.16 C.51.1022 B.17 C.5 1.1023 B.18 C.5 1.1024 B.19 C.5 1.1025 B.20 C.5 1.1026B.21 C.5 1.1027 B.22 C.5 1.1028 B.23 C.5 1.1029 B.24 C.5 1.1030 B.25 C.51.1031 B.26 C.5 1.1032 B.27 C.5 1.1033 B.28 C.5 1.1034 B.29 C.5 1.1035B.30 C.5 1.1036 B.31 C.5 1.1037 B.32 C.5 1.1038 B.33 C.5 1.1039 B.34 C.51.1040 B.35 C.5 1.1041 B.36 C.5 1.1042 B.37 C.5 1.1043 B.38 C.5 1.1044B.39 C.5 1.1045 B.40 C.5 1.1046 B.41 C.5 1.1047 B.42 C.5 1.1048 B.43 C.51.1049 B.44 C.5 1.1050 B.45 C.5 1.1051 B.46 C.5 1.1052 B.47 C.5 1.1053B.48 C.5 1.1054 B.49 C.5 1.1055 B.50 C.5 1.1056 B.51 C.5 1.1057 B.52 C.51.1058 B.53 C.5 1.1059 B.54 C.5 1.1060 B.55 C.5 1.1061 B.56 C.5 1.1062B.57 C.5 1.1063 B.58. C.5 1.1064 B.59 C.5 1.1065 B.60 C.5 1.1066 B.61C.5 1.1067 B.62 C.5 1.1068 B.63 C.5 1.1069 B.64 C.5 1.1070 B.65 C.51.1071 B.66 C.5 1.1072 B.67 C.5 1.1073 B.68 C.5 1.1074 B.69 C.5 1.1075B.70 C.5 1.1076 B.71 C.5 1.1077 B.72 C.5 1.1078 B.73 C.5 1.1079 B.74 C.51.1080 B.75 C.5 1.1081 B.76 C.5 1.1082 B.77 C.5 1.1083 B.78 C.5 1.1084B.79 C.5 1.1085 B.80 C.5 1.1086 B.81 C.5 1.1087 B.82 C.5 1.1088 B.83 C.51.1089 B.84 C.5 1.1090 B.85 C.5 1.1091 B.86 C.5 1.1092 B.87 C.5 1.1093B.88 C.5 1.1094 B.89 C.5 1.1095 B.90 C.5 1.1096 B.91 C.5 1.1097 B.92 C.51.1098 B.93 C.5 1.1099 B.94 C.5 1.1100 B.95 C.5 1.1101 B.96 C.5 1.1102B.97 C.5 1.1103 B.98 C.5 1.1104 B.99 C.5 1.1105 B.100 C.5 1.1106 B.101C.5 1.1107 B.102 C.5 1.1108 B.103 C.5 1.1109 B.104 C.5 1.1110 B.105 C.51.1111 B.106 C.5 1.1112 B.107 C.5 1.1113 B.108 C.5 1.1114 B.109 C.51.1115 B.110 C.5 1.1116 B.111 C.5 1.1117 B.112 C.5 1.1118 B.113 C.51.1119 B.114 C.5 1.1120 B.115 C.5 1.1121 B.116 C.5 1.1122 B.117 C.51.1123 B.118 C.5 1.1124 B.119 C.5 1.1125 B.120 C.5 1.1126 B.121 C.51.1127 B.122 C.5 1.1128 B.123 C.5 1.1129 B.124 C.5 1.1130 B.125 C.51.1131 B.126 C.5 1.1132 B.127 C.5 1.1133 B.128 C.5 1.1134 B.129 C.51.1135 B.130 C.5 1.1136 B.131 C.5 1.1137 B.132 C.5 1.1138 B.133 C.51.1139 B.134 C.5 1.1140 B.135 C.5 1.1141 B.136 C.5 1.1142 B.137 C.51.1143 B.138 C.5 1.1144 B.139 C.5 1.1145 B.140 C.5 1.1146 B.141 C.51.1147 B.142 C.5 1.1148 B.143 C.5 1.1149 B.144 C.5 1.1150 B.145 C.51.1151 B.146 C.5 1.1152 B.147 C.5 1.1153 B.148 C.5 1.1154 B.149 C.51.1155 B.150 C.5 1.1156 B.151 C.5 1.1157 B.152 C.5 1.1158 B.153 C.51.1159 B.154 C.5 1.1160 B.155 C.5 1.1161 B.156 C.5 1.1162 B.157 C.51.1163 B.158 C.5 1.1164 B.159 C.5 1.1165 B.160 C.5 1.1166 B.161 C.51.1167 B.162 C.5 1.1168 B.163 C.5 1.1169 B.164 C.5 1.1170 B.165 C.51.1171 B.166 C.5 1.1172 B.167 C.5 1.1173 B.168 C.5 1.1174 B.169 C.51.1175 B.170 C.5 1.1176 B.171 C.5 1.1177 B.172 C.5 1.1178 B.173 C.51.1179 B.174 C.5 1.1180 B.175 C.5 1.1181 B.176 C.5 1.1182 B.177 C.51.1183 B.178 C.5 1.1184 B.179 C.5 1.1185 B.180 C.5 1.1186 B.181 C.51.1187 B.182 C.5 1.1188 B.183 C.5 1.1189 B.184 C.5 1.1190 B.185 C.51.1191 B.186 C.5 1.1192 B.187 C.5 1.1193 B.188 C.5 1.1194 B.189 C.51.1195 B.190 C.5 1.1196 B.191 C.5 1.1197 B.192 C.5 1.1198 B.193 C.51.1199 B.194 C.5 1.1200 B.195 C.5 1.1201 B.196 C.5 1.1202 B.197 C.51.1203 B.198 C.5 1.1204 B.199 C.5 1.1205 B.200 C.5 1.1206 B.201 C.51.1207 B.1 C.6 1.1208 B.2 C.6 1.1209 B.3 C.6 1.1210 B.4 C.6 1.1211 B.5C.6 1.1212 B.6 C.6 1.1213 B.7 C.6 1.1214 B.8 C.6 1.1215 B.9 C.6 1.1216B.10 C.6 1.1217 B.11 C.6 1.1218 B.12 C.6 1.1219 B.13 C.6 1.1220 B.14 C.61.1221 B.15 C.6 1.1222 B.16 C.6 1.1223 B.17 C.6 1.1224 B.18 C.6 1.1225B.19 C.6 1.1226 B.20 C.6 1.1227 B.21 C.6 1.1228 B.22 C.6 1.1229 B.23 C.61.1230 B.24 C.6 1.1231 B.25 C.6 1.1232 B.26 C.6 1.1233 B.27 C.6 1.1234B.28 C.6 1.1235 B.29 C.6 1.1236 B.30 C.6 1.1237 B.31 C.6 1.1238 B.32 C.61.1239 B.33 C.6 1.1240 B.34 C.6 1.1241 B.35 C.6 1.1242 B.36 C.6 1.1243B.37 C.6 1.1244 B.38 C.6 1.1245 B.39 C.6 1.1246 B.40 C.6 1.1247 B.41 C.61.1248 B.42 C.6 1.1249 B.43 C.6 1.1250 B.44 C.6 1.1251 B.45 C.6 1.1252B.46 C.6 1.1253 B.47 C.6 1.1254 B.48 C.6 1.1255 B.49 C.6 1.1256 B.50 C.61.1257 B.51 C.6 1.1258 B.52 C.6 1.1259 B.53 C.6 1.1260 B.54 C.6 1.1261B.55 C.6 1.1262 B.56 C.6 1.1263 B.57 C.6 1.1264 B.58. C.6 1.1265 B.59C.6 1.1266 B.60 C.6 1.1267 B.61 C.6 1.1268 B.62 C.6 1.1269 B.63 C.61.1270 B.64 C.6 1.1271 B.65 C.6 1.1272 B.66 C.6 1.1273 B.67 C.6 1.1274B.68 C.6 1.1275 B.69 C.6 1.1276 B.70 C.6 1.1277 B.71 C.6 1.1278 B.72 C.61.1279 B.73 C.6 1.1280 B.74 C.6 1.1281 B.75 C.6 1.1282 B.76 C.6 1.1283B.77 C.6 1.1284 B.78 C.6 1.1285 B.79 C.6 1.1286 B.80 C.6 1.1287 B.81 C.61.1288 B.82 C.6 1.1289 B.83 C.6 1.1290 B.84 C.6 1.1291 B.85 C.6 1.1292B.86 C.6 1.1293 B.87 C.6 1.1294 B.88 C.6 1.1295 B.89 C.6 1.1296 B.90 C.61.1297 B.91 C.6 1.1298 B.92 C.6 1.1299 B.93 C.6 1.1300 B.94 C.6 1.1301B.95 C.6 1.1302 B.96 C.6 1.1303 B.97 C.6 1.1304 B.98 C.6 1.1305 B.99 C.61.1306 B.100 C.6 1.1307 B.101 C.6 1.1308 B.102 C.6 1.1309 B.103 C.61.1310 B.104 C.6 1.1311 B.105 C.6 1.1312 B.106 C.6 1.1313 B.107 C.61.1314 B.108 C.6 1.1315 B.109 C.6 1.1316 B.110 C.6 1.1317 B.111 C.61.1318 B.112 C.6 1.1319 B.113 C.6 1.1320 B.114 C.6 1.1321 B.115 C.61.1322 B.116 C.6 1.1323 B.117 C.6 1.1324 B.118 C.6 1.1325 B.119 C.61.1326 B.120 C.6 1.1327 B.121 C.6 1.1328 B.122 C.6 1.1329 B.123 C.61.1330 B.124 C.6 1.1331 B.125 C.6 1.1332 B.126 C.6 1.1333 B.127 C.61.1334 B.128 C.6 1.1335 B.129 C.6 1.1336 B.130 C.6 1.1337 B.131 C.61.1338 B.132 C.6 1.1339 B.133 C.6 1.1340 B.134 C.6 1.1341 B.135 C.61.1342 B.136 C.6 1.1343 B.137 C.6 1.1344 B.138 C.6 1.1345 B.139 C.61.1346 B.140 C.6 1.1347 B.141 C.6 1.1348 B.142 C.6 1.1349 B.143 C.61.1350 B.144 C.6 1.1351 B.145 C.6 1.1352 B.146 C.6 1.1353 B.147 C.61.1354 B.148 C.6 1.1355 B.149 C.6 1.1356 B.150 C.6 1.1357 B.151 C.61.1358 B.152 C.6 1.1359 B.153 C.6 1.1360 B.154 C.6 1.1361 B.155 C.61.1362 B.156 C.6 1.1363 B.157 C.6 1.1364 B.158 C.6 1.1365 B.159 C.61.1366 B.160 C.6 1.1367 B.161 C.6 1.1368 B.162 C.6 1.1369 B.163 C.61.1370 B.164 C.6 1.1371 B.165 C.6 1.1372 B.166 C.6 1.1373 B.167 C.61.1374 B.168 C.6 1.1375 B.169 C.6 1.1376 B.170 C.6 1.1377 B.171 C.61.1378 B.172 C.6 1.1379 B.173 C.6 1.1380 B.174 C.6 1.1381 B.175 C.61.1382 B.176 C.6 1.1383 B.177 C.6 1.1384 B.178 C.6 1.1385 B.179 C.61.1386 B.180 C.6 1.1387 B.181 C.6 1.1388 B.182 C.6 1.1389 B.183 C.61.1390 B.184 C.6 1.1391 B.185 C.6 1.1392 B.186 C.6 1.1393 B.187 C.61.1394 B.188 C.6 1.1395 B.189 C.6 1.1396 B.190 C.6 1.1397 B.191 C.61.1398 B.192 C.6 1.1399 B.193 C.6 1.1400 B.194 C.6 1.1401 B.195 C.61.1402 B.196 C.6 1.1403 B.197 C.6 1.1404 B.198 C.6 1.1405 B.199 C.61.1406 B.200 C.6 1.1407 B.201 C.6 1.1408 B.1 C.7 1.1409 B.2 C.7 1.1410B.3 C.7 1.1411 B.4 C.7 1.1412 B.5 C.7 1.1413 B.6 C.7 1.1414 B.7 C.71.1415 B.8 C.7 1.1416 B.9 C.7 1.1417 B.10 C.7 1.1418 B.11 C.7 1.1419B.12 C.7 1.1420 B.13 C.7 1.1421 B.14 C.7 1.1422 B.15 C.7 1.1423 B.16 C.71.1424 B.17 C.7 1.1425 B.18 C.7 1.1426 B.19 C.7 1.1427 B.20 C.7 1.1428B.21 C.7 1.1429 B.22 C.7 1.1430 B.23 C.7 1.1431 B.24 C.7 1.1432 B.25 C.71.1433 B.26 C.7 1.1434 B.27 C.7 1.1435 B.28 C.7 1.1436 B.29 C.7 1.1437B.30 C.7 1.1438 B.31 C.7 1.1439 B.32 C.7 1.1440 B.33 C.7 1.1441 B.34 C.71.1442 B.35 C.7 1.1443 B.36 C.7 1.1444 B.37 C.7 1.1445 B.38 C.7 1.1446B.39 C.7 1.1447 B.40 C.7 1.1448 B.41 C.7 1.1449 B.42 C.7 1.1450 B.43 C.71.1451 B.44 C.7 1.1452 B.45 C.7 1.1453 B.46 C.7 1.1454 B.47 C.7 1.1455B.48 C.7 1.1456 B.49 C.7 1.1457 B.50 C.7 1.1458 B.51 C.7 1.1459 B.52 C.71.1460 B.53 C.7 1.1461 B.54 C.7 1.1462 B.55 C.7 1.1463 B.56 C.7 1.1464B.57 C.7 1.1465 B.58. C.7 1.1466 B.59 C.7 1.1467 B.60 C.7 1.1468 B.61C.7 1.1469 B.62 C.7 1.1470 B.63 C.7 1.1471 B.64 C.7 1.1472 B.65 C.71.1473 B.66 C.7 1.1474 B.67 C.7 1.1475 B.68 C.7 1.1476 B.69 C.7 1.1477B.70 C.7 1.1478 B.71 C.7 1.1479 B.72 C.7 1.1480 B.73 C.7 1.1481 B.74 C.71.1482 B.75 C.7 1.1483 B.76 C.7 1.1484 B.77 C.7 1.1485 B.78 C.7 1.1486B.79 C.7 1.1487 B.80 C.7 1.1488 B.81 C.7 1.1489 B.82 C.7 1.1490 B.83 C.71.1491 B.84 C.7 1.1492 B.85 C.7 1.1493 B.86 C.7 1.1494 B.87 C.7 1.1495B.88 C.7 1.1496 B.89 C.7 1.1497 B.90 C.7 1.1498 B.91 C.7 1.1499 B.92 C.71.1500 B.93 C.7 1.1501 B.94 C.7 1.1502 B.95 C.7 1.1503 B.96 C.7 1.1504B.97 C.7 1.1505 B.98 C.7 1.1506 B.99 C.7 1.1507 B.100 C.7 1.1508 B.101C.7 1.1509 B.102 C.7 1.1510 B.103 C.7 1.1511 B.104 C.7 1.1512 B.105 C.71.1513 B.106 C.7 1.1514 B.107 C.7 1.1515 B.108 C.7 1.1516 B.109 C.71.1517 B.110 C.7 1.1518 B.111 C.7 1.1519 B.112 C.7 1.1520 B.113 C.71.1521 B.114 C.7 1.1522 B.115 C.7 1.1523 B.116 C.7 1.1524 B.117 C.71.1525 B.118 C.7 1.1526 B.119 C.7 1.1527 B.120 C.7 1.1528 B.121 C.71.1529 B.122 C.7 1.1530 B.123 C.7 1.1531 B.124 C.7 1.1532 B.125 C.71.1533 B.126 C.7 1.1534 B.127 C.7 1.1535 B.128 C.7 1.1536 B.129 C.71.1537 B.130 C.7 1.1538 B.131 C.7 1.1539 B.132 C.7 1.1540 B.133 C.71.1541 B.134 C.7 1.1542 B.135 C.7 1.1543 B.136 C.7 1.1544 B.137 C.71.1545 B.138 C.7 1.1546 B.139 C.7 1.1547 B.140 C.7 1.1548 B.141 C.71.1549 B.142 C.7 1.1550 B.143 C.7 1.1551 B.144 C.7 1.1552 B.145 C.71.1553 B.146 C.7 1.1554 B.147 C.7 1.1555 B.148 C.7 1.1556 B.149 C.71.1557 B.150 C.7 1.1558 B.151 C.7 1.1559 B.152 C.7 1.1560 B.153 C.71.1561 B.154 C.7 1.1562 B.155 C.7 1.1563 B.156 C.7 1.1564 B.157 C.71.1565 B.158 C.7 1.1566 B.159 C.7 1.1567 B.160 C.7 1.1568 B.161 C.71.1569 B.162 C.7 1.1570 B.163 C.7 1.1571 B.164 C.7 1.1572 B.165 C.71.1573 B.166 C.7 1.1574 B.167 C.7 1.1575 B.168 C.7 1.1576 B.169 C.71.1577 B.170 C.7 1.1578 B.171 C.7 1.1579 B.172 C.7 1.1580 B.173 C.71.1581 B.174 C.7 1.1582 B.175 C.7 1.1583 B.176 C.7 1.1584 B.177 C.71.1585 B.178 C.7 1.1586 B.179 C.7 1.1587 B.180 C.7 1.1588 B.181 C.71.1589 B.182 C.7 1.1590 B.183 C.7 1.1591 B.184 C.7 1.1592 B.185 C.71.1593 B.186 C.7 1.1594 B.187 C.7 1.1595 B.188 C.7 1.1596 B.189 C.71.1597 B.190 C.7 1.1598 B.191 C.7 1.1599 B.192 C.7 1.1600 B.193 C.71.1601 B.194 C.7 1.1602 B.195 C.7 1.1603 B.196 C.7 1.1604 B.197 C.71.1605 B.198 C.7 1.1606 B.199 C.7 1.1607 B.200 C.7 1.1608 B.201 C.71.1609 B.1 C.8 1.1610 B.2 C.8 1.1611 B.3 C.8 1.1612 B.4 C.8 1.1613 B.5C.8 1.1614 B.6 C.8 1.1615 B.7 C.8 1.1616 B.8 C.8 1.1617 B.9 C.8 1.1618B.10 C.8 1.1619 B.11 C.8 1.1620 B.12 C.8 1.1621 B.13 C.8 1.1622 B.14 C.81.1623 B.15 C.8 1.1624 B.16 C.8 1.1625 B.17 C.8 1.1626 B.18 C.8 1.1627B.19 C.8 1.1628 B.20 C.8 1.1629 B.21 C.8 1.1630 B.22 C.8 1.1631 B.23 C.81.1632 B.24 C.8 1.1633 B.25 C.8 1.1634 B.26 C.8 1.1635 B.27 C.8 1.1636B.28 C.8 1.1637 B.29 C.8 1.1638 B.30 C.8 1.1639 B.31 C.8 1.1640 B.32 C.81.1641 B.33 C.8 1.1642 B.34 C.8 1.1643 B.35 C.8 1.1644 B.36 C.8 1.1645B.37 C.8 1.1646 B.38 C.8 1.1647 B.39 C.8 1.1648 B.40 C.8 1.1649 B.41 C.81.1650 B.42 C.8 1.1651 B.43 C.8 1.1652 B.44 C.8 1.1653 B.45 C.8 1.1654B.46 C.8 1.1655 B.47 C.8 1.1656 B.48 C.8 1.1657 B.49 C.8 1.1658 B.50 C.81.1659 B.51 C.8 1.1660 B.52 C.8 1.1661 B.53 C.8 1.1662 B.54 C.8 1.1663B.55 C.8 1.1664 B.56 C.8 1.1665 B.57 C.8 1.1666 B.58. C.8 1.1667 B.59C.8 1.1668 B.60 C.8 1.1669 B.61 C.8 1.1670 B.62 C.8 1.1671 B.63 C.81.1672 B.64 C.8 1.1673 B.65 C.8 1.1674 B.66 C.8 1.1675 B.67 C.8 1.1676B.68 C.8 1.1677 B.69 C.8 1.1678 B.70 C.8 1.1679 B.71 C.8 1.1680 B.72 C.81.1681 B.73 C.8 1.1682 B.74 C.8 1.1683 B.75 C.8 1.1684 B.76 C.8 1.1685B.77 C.8 1.1686 B.78 C.8 1.1687 B.79 C.8 1.1688 B.80 C.8 1.1689 B.81 C.81.1690 B.82 C.8 1.1691 B.83 C.8 1.1692 B.84 C.8 1.1693 B.85 C.8 1.1694B.86 C.8 1.1695 B.87 C.8 1.1696 B.88 C.8 1.1697 B.89 C.8 1.1698 B.90 C.81.1699 B.91 C.8 1.1700 B.92 C.8 1.1701 B.93 C.8 1.1702 B.94 C.8 1.1703B.95 C.8 1.1704 B.96 C.8 1.1705 B.97 C.8 1.1706 B.98 C.8 1.1707 B.99 C.81.1708 B.100 C.8 1.1709 B.101 C.8 1.1710 B.102 C.8 1.1711 B.103 C.81.1712 B.104 C.8 1.1713 B.105 C.8 1.1714 B.106 C.8 1.1715 B.107 C.81.1716 B.108 C.8 1.1717 B.109 C.8 1.1718 B.110 C.8 1.1719 B.111 C.81.1720 B.112 C.8 1.1721 B.113 C.8 1.1722 B.114 C.8 1.1723 B.115 C.81.1724 B.116 C.8 1.1725 B.117 C.8 1.1726 B.118 C.8 1.1727 B.119 C.81.1728 B.120 C.8 1.1729 B.121 C.8 1.1730 B.122 C.8 1.1731 B.123 C.81.1732 B.124 C.8 1.1733 B.125 C.8 1.1734 B.126 C.8 1.1735 B.127 C.81.1736 B.128 C.8 1.1737 B.129 C.8 1.1738 B.130 C.8 1.1739 B.131 C.81.1740 B.132 C.8 1.1741 B.133 C.8 1.1742 B.134 C.8 1.1743 B.135 C.81.1744 B.136 C.8 1.1745 B.137 C.8 1.1746 B.138 C.8 1.1747 B.139 C.81.1748 B.140 C.8 1.1749 B.141 C.8 1.1750 B.142 C.8 1.1751 B.143 C.81.1752 B.144 C.8 1.1753 B.145 C.8 1.1754 B.146 C.8 1.1755 B.147 C.81.1756 B.148 C.8 1.1757 B.149 C.8 1.1758 B.150 C.8 1.1759 B.151 C.81.1760 B.152 C.8 1.1761 B.153 C.8 1.1762 B.154 C.8 1.1763 B.155 C.81.1764 B.156 C.8 1.1765 B.157 C.8 1.1766 B.158 C.8 1.1767 B.159 C.81.1768 B.160 C.8 1.1769 B.161 C.8 1.1770 B.162 C.8 1.1771 B.163 C.81.1772 B.164 C.8 1.1773 B.165 C.8 1.1774 B.166 C.8 1.1775 B.167 C.81.1776 B.168 C.8 1.1777 B.169 C.8 1.1778 B.170 C.8 1.1779 B.171 C.81.1780 B.172 C.8 1.1781 B.173 C.8 1.1782 B.174 C.8 1.1783 B.175 C.81.1784 B.176 C.8 1.1785 B.177 C.8 1.1786 B.178 C.8 1.1787 B.179 C.81.1788 B.180 C.8 1.1789 B.181 C.8 1.1790 B.182 C.8 1.1791 B.183 C.81.1792 B.184 C.8 1.1793 B.185 C.8 1.1794 B.186 C.8 1.1795 B.187 C.81.1796 B.188 C.8 1.1797 B.189 C.8 1.1798 B.190 C.8 1.1799 B.191 C.81.1800 B.192 C.8 1.1801 B.193 C.8 1.1802 B.194 C.8 1.1803 B.195 C.81.1804 B.196 C.8 1.1805 B.197 C.8 1.1806 B.198 C.8 1.1807 B.199 C.81.1808 B.200 C.8 1.1809 B.201 C.8 1.1810 B.1 C.9 1.1811 B.2 C.9 1.1812B.3 C.9 1.1813 B.4 C.9 1.1814 B.5 C.9 1.1815 B.6 C.9 1.1816 B.7 C.91.1817 B.8 C.9 1.1818 B.9 C.9 1.1819 B.10 C.9 1.1820 B.11 C.9 1.1821B.12 C.9 1.1822 B.13 C.9 1.1823 B.14 C.9 1.1824 B.15 C.9 1.1825 B.16 C.91.1826 B.17 C.9 1.1827 B.18 C.9 1.1828 B.19 C.9 1.1829 B.20 C.9 1.1830B.21 C.9 1.1831 B.22 C.9 1.1832 B.23 C.9 1.1833 B.24 C.9 1.1834 B.25 C.91.1835 B.26 C.9 1.1836 B.27 C.9 1.1837 B.28 C.9 1.1838 B.29 C.9 1.1839B.30 C.9 1.1840 B.31 C.9 1.1841 B.32 C.9 1.1842 B.33 C.9 1.1843 B.34 C.91.1844 B.35 C.9 1.1845 B.36 C.9 1.1846 B.37 C.9 1.1847 B.38 C.9 1.1848B.39 C.9 1.1849 B.40 C.9 1.1850 B.41 C.9 1.1851 B.42 C.9 1.1852 B.43 C.91.1853 B.44 C.9 1.1854 B.45 C.9 1.1855 B.46 C.9 1.1856 B.47 C.9 1.1857B.48 C.9 1.1858 B.49 C.9 1.1859 B.50 C.9 1.1860 B.51 C.9 1.1861 B.52 C.91.1862 B.53 C.9 1.1863 B.54 C.9 1.1864 B.55 C.9 1.1865 B.56 C.9 1.1866B.57 C.9 1.1867 B.58. C.9 1.1868 B.59 C.9 1.1869 B.60 C.9 1.1870 B.61C.9 1.1871 B.62 C.9 1.1872 B.63 C.9 1.1873 B.64 C.9 1.1874 B.65 C.91.1875 B.66 C.9 1.1876 B.67 C.9 1.1877 B.68 C.9 1.1878 B.69 C.9 1.1879B.70 C.9 1.1880 B.71 C.9 1.1881 B.72 C.9 1.1882 B.73 C.9 1.1883 B.74 C.91.1884 B.75 C.9 1.1885 B.76 C.9 1.1886 B.77 C.9 1.1887 B.78 C.9 1.1888B.79 C.9 1.1889 B.80 C.9 1.1890 B.81 C.9 1.1891 B.82 C.9 1.1892 B.83 C.91.1893 B.84 C.9 1.1894 B.85 C.9 1.1895 B.86 C.9 1.1896 B.87 C.9 1.1897B.88 C.9 1.1898 B.89 C.9 1.1899 B.90 C.9 1.1900 B.91 C.9 1.1901 B.92 C.91.1902 B.93 C.9 1.1903 B.94 C.9 1.1904 B.95 C.9 1.1905 B.96 C.9 1.1906B.97 C.9 1.1907 B.98 C.9 1.1908 B.99 C.9 1.1909 B.100 C.9 1.1910 B.101C.9 1.1911 B.102 C.9 1.1912 B.103 C.9 1.1913 B.104 C.9 1.1914 B.105 C.91.1915 B.106 C.9 1.1916 B.107 C.9 1.1917 B.108 C.9 1.1918 B.109 C.91.1919 B.110 C.9 1.1920 B.111 C.9 1.1921 B.112 C.9 1.1922 B.113 C.91.1923 B.114 C.9 1.1924 B.115 C.9 1.1925 B.116 C.9 1.1926 B.117 C.91.1927 B.118 C.9 1.1928 B.119 C.9 1.1929 B.120 C.9 1.1930 B.121 C.91.1931 B.122 C.9 1.1932 B.123 C.9 1.1933 B.124 C.9 1.1934 B.125 C.91.1935 B.126 C.9 1.1936 B.127 C.9 1.1937 B.128 C.9 1.1938 B.129 C.91.1939 B.130 C.9 1.1940 B.131 C.9 1.1941 B.132 C.9 1.1942 B.133 C.91.1943 B.134 C.9 1.1944 B.135 C.9 1.1945 B.136 C.9 1.1946 B.137 C.91.1947 B.138 C.9 1.1948 B.139 C.9 1.1949 B.140 C.9 1.1950 B.141 C.91.1951 B.142 C.9 1.1952 B.143 C.9 1.1953 B.144 C.9 1.1954 B.145 C.91.1955 B.146 C.9 1.1956 B.147 C.9 1.1957 B.148 C.9 1.1958 B.149 C.91.1959 B.150 C.9 1.1960 B.151 C.9 1.1961 B.152 C.9 1.1962 B.153 C.91.1963 B.154 C.9 1.1964 B.155 C.9 1.1965 B.156 C.9 1.1966 B.157 C.91.1967 B.158 C.9 1.1968 B.159 C.9 1.1969 B.160 C.9 1.1970 B.161 C.91.1971 B.162 C.9 1.1972 B.163 C.9 1.1973 B.164 C.9 1.1974 B.165 C.91.1975 B.166 C.9 1.1976 B.167 C.9 1.1977 B.168 C.9 1.1978 B.169 C.91.1979 B.170 C.9 1.1980 B.171 C.9 1.1981 B.172 C.9 1.1982 B.173 C.91.1983 B.174 C.9 1.1984 B.175 C.9 1.1985 B.176 C.9 1.1986 B.177 C.91.1987 B.178 C.9 1.1988 B.179 C.9 1.1989 B.180 C.9 1.1990 B.181 C.91.1991 B.182 C.9 1.1992 B.183 C.9 1.1993 B.184 C.9 1.1994 B.185 C.91.1995 B.186 C.9 1.1996 B.187 C.9 1.1997 B.188 C.9 1.1998 B.189 C.91.1999 B.190 C.9 1.2000 B.191 C.9 1.2001 B.192 C.9 1.2002 B.193 C.91.2003 B.194 C.9 1.2004 B.195 C.9 1.2005 B.196 C.9 1.2006 B.197 C.91.2007 B.198 C.9 1.2008 B.199 C.9 1.2009 B.200 C.9 1.2010 B.201 C.91.2011 B.1 C.10 1.2012 B.2 C.10 1.2013 B.3 C.10 1.2014 B.4 C.10 1.2015B.5 C.10 1.2016 B.6 C.10 1.2017 B.7 C.10 1.2018 B.8 C.10 1.2019 B.9 C.101.2020 B.10 C.10 1.2021 B.11 C.10 1.2022 B.12 C.10 1.2023 B.13 C.101.2024 B.14 C.10 1.2025 B.15 C.10 1.2026 B.16 C.10 1.2027 B.17 C.101.2028 B.18 C.10 1.2029 B.19 C.10 1.2030 B.20 C.10 1.2031 B.21 C.101.2032 B.22 C.10 1.2033 B.23 C.10 1.2034 B.24 C.10 1.2035 B.25 C.101.2036 B.26 C.10 1.2037 B.27 C.10 1.2038 B.28 C.10 1.2039 B.29 C.101.2040 B.30 C.10 1.2041 B.31 C.10 1.2042 B.32 C.10 1.2043 B.33 C.101.2044 B.34 C.10 1.2045 B.35 C.10 1.2046 B.36 C.10 1.2047 B.37 C.101.2048 B.38 C.10 1.2049 B.39 C.10 1.2050 B.40 C.10 1.2051 B.41 C.101.2052 B.42 C.10 1.2053 B.43 C.10 1.2054 B.44 C.10 1.2055 B.45 C.101.2056 B.46 C.10 1.2057 B.47 C.10 1.2058 B.48 C.10 1.2059 B.49 C.101.2060 B.50 C.10 1.2061 B.51 C.10 1.2062 B.52 C.10 1.2063 B.53 C.101.2064 B.54 C.10 1.2065 B.55 C.10 1.2066 B.56 C.10 1.2067 B.57 C.101.2068 B.58. C.10 1.2069 B.59 C.10 1.2070 B.60 C.10 1.2071 B.61 C.101.2072 B.62 C.10 1.2073 B.63 C.10 1.2074 B.64 C.10 1.2075 B.65 C.101.2076 B.66 C.10 1.2077 B.67 C.10 1.2078 B.68 C.10 1.2079 B.69 C.101.2080 B.70 C.10 1.2081 B.71 C.10 1.2082 B.72 C.10 1.2083 B.73 C.101.2084 B.74 C.10 1.2085 B.75 C.10 1.2086 B.76 C.10 1.2087 B.77 C.101.2088 B.78 C.10 1.2089 B.79 C.10 1.2090 B.80 C.10 1.2091 B.81 C.101.2092 B.82 C.10 1.2093 B.83 C.10 1.2094 B.84 C.10 1.2095 B.85 C.101.2096 B.86 C.10 1.2097 B.87 C.10 1.2098 B.88 C.10 1.2099 B.89 C.101.2100 B.90 C.10 1.2101 B.91 C.10 1.2102 B.92 C.10 1.2103 B.93 C.101.2104 B.94 C.10 1.2105 B.95 C.10 1.2106 B.96 C.10 1.2107 B.97 C.101.2108 B.98 C.10 1.2109 B.99 C.10 1.2110 B.100 C.10 1.2111 B.101 C.101.2112 B.102 C.10 1.2113 B.103 C.10 1.2114 B.104 C.10 1.2115 B.105 C.101.2116 B.106 C.10 1.2117 B.107 C.10 1.2118 B.108 C.10 1.2119 B.109 C.101.2120 B.110 C.10 1.2121 B.111 C.10 1.2122 B.112 C.10 1.2123 B.113 C.101.2124 B.114 C.10 1.2125 B.115 C.10 1.2126 B.116 C.10 1.2127 B.117 C.101.2128 B.118 C.10 1.2129 B.119 C.10 1.2130 B.120 C.10 1.2131 B.121 C.101.2132 B.122 C.10 1.2133 B.123 C.10 1.2134 B.124 C.10 1.2135 B.125 C.101.2136 B.126 C.10 1.2137 B.127 C.10 1.2138 B.128 C.10 1.2139 B.129 C.101.2140 B.130 C.10 1.2141 B.131 C.10 1.2142 B.132 C.10 1.2143 B.133 C.101.2144 B.134 C.10 1.2145 B.135 C.10 1.2146 B.136 C.10 1.2147 B.137 C.101.2148 B.138 C.10 1.2149 B.139 C.10 1.2150 B.140 C.10 1.2151 B.141 C.101.2152 B.142 C.10 1.2153 B.143 C.10 1.2154 B.144 C.10 1.2155 B.145 C.101.2156 B.146 C.10 1.2157 B.147 C.10 1.2158 B.148 C.10 1.2159 B.149 C.101.2160 B.150 C.10 1.2161 B.151 C.10 1.2162 B.152 C.10 1.2163 B.153 C.101.2164 B.154 C.10 1.2165 B.155 C.10 1.2166 B.156 C.10 1.2167 B.157 C.101.2168 B.158 C.10 1.2169 B.159 C.10 1.2170 B.160 C.10 1.2171 B.161 C.101.2172 B.162 C.10 1.2173 B.163 C.10 1.2174 B.164 C.10 1.2175 B.165 C.101.2176 B.166 C.10 1.2177 B.167 C.10 1.2178 B.168 C.10 1.2179 B.169 C.101.2180 B.170 C.10 1.2181 B.171 C.10 1.2182 B.172 C.10 1.2183 B.173 C.101.2184 B.174 C.10 1.2185 B.175 C.10 1.2186 B.176 C.10 1.2187 B.177 C.101.2188 B.178 C.10 1.2189 B.179 C.10 1.2190 B.180 C.10 1.2191 B.181 C.101.2192 B.182 C.10 1.2193 B.183 C.10 1.2194 B.184 C.10 1.2195 B.185 C.101.2196 B.186 C.10 1.2197 B.187 C.10 1.2198 B.188 C.10 1.2199 B.189 C.101.2200 B.190 C.10 1.2201 B.191 C.10 1.2202 B.192 C.10 1.2203 B.193 C.101.2204 B.194 C.10 1.2205 B.195 C.10 1.2206 B.196 C.10 1.2207 B.197 C.101.2208 B.198 C.10 1.2209 B.199 C.10 1.2210 B.200 C.10 1.2211 B.201 C.101.2212 B.1 C.11 1.2213 B.2 C.11 1.2214 B.3 C.11 1.2215 B.4 C.11 1.2216B.5 C.11 1.2217 B.6 C.11 1.2218 B.7 C.11 1.2219 B.8 C.11 1.2220 B.9 C.111.2221 B.10 C.11 1.2222 B.11 C.11 1.2223 B.12 C.11 1.2224 B.13 C.111.2225 B.14 C.11 1.2226 B.15 C.11 1.2227 B.16 C.11 1.2228 B.17 C.111.2229 B.18 C.11 1.2230 B.19 C.11 1.2231 B.20 C.11 1.2232 B.21 C.111.2233 B.22 C.11 1.2234 B.23 C.11 1.2235 B.24 C.11 1.2236 B.25 C.111.2237 B.26 C.11 1.2238 B.27 C.11 1.2239 B.28 C.11 1.2240 B.29 C.111.2241 B.30 C.11 1.2242 B.31 C.11 1.2243 B.32 C.11 1.2244 B.33 C.111.2245 B.34 C.11 1.2246 B.35 C.11 1.2247 B.36 C.11 1.2248 B.37 C.111.2249 B.38 C.11 1.2250 B.39 C.11 1.2251 B.40 C.11 1.2252 B.41 C.111.2253 B.42 C.11 1.2254 B.43 C.11 1.2255 B.44 C.11 1.2256 B.45 C.111.2257 B.46 C.11 1.2258 B.47 C.11 1.2259 B.48 C.11 1.2260 B.49 C.111.2261 B.50 C.11 1.2262 B.51 C.11 1.2263 B.52 C.11 1.2264 B.53 C.111.2265 B.54 C.11 1.2266 B.55 C.11 1.2267 B.56 C.11 1.2268 B.57 C.111.2269 B.58. C.11 1.2270 B.59 C.11 1.2271 B.60 C.11 1.2272 B.61 C.111.2273 B.62 C.11 1.2274 B.63 C.11 1.2275 B.64 C.11 1.2276 B.65 C.111.2277 B.66 C.11 1.2278 B.67 C.11 1.2279 B.68 C.11 1.2280 B.69 C.111.2281 B.70 C.11 1.2282 B.71 C.11 1.2283 B.72 C.11 1.2284 B.73 C.111.2285 B.74 C.11 1.2286 B.75 C.11 1.2287 B.76 C.11 1.2288 B.77 C.111.2289 B.78 C.11 1.2290 B.79 C.11 1.2291 B.80 C.11 1.2292 B.81 C.111.2293 B.82 C.11 1.2294 B.83 C.11 1.2295 B.84 C.11 1.2296 B.85 C.111.2297 B.86 C.11 1.2298 B.87 C.11 1.2299 B.88 C.11 1.2300 B.89 C.111.2301 B.90 C.11 1.2302 B.91 C.11 1.2303 B.92 C.11 1.2304 B.93 C.111.2305 B.94 C.11 1.2306 B.95 C.11 1.2307 B.96 C.11 1.2308 B.97 C.111.2309 B.98 C.11 1.2310 B.99 C.11 1.2311 B.100 C.11 1.2312 B.101 C.111.2313 B.102 C.11 1.2314 B.103 C.11 1.2315 B.104 C.11 1.2316 B.105 C.111.2317 B.106 C.11 1.2318 B.107 C.11 1.2319 B.108 C.11 1.2320 B.109 C.111.2321 B.110 C.11 1.2322 B.111 C.11 1.2323 B.112 C.11 1.2324 B.113 C.111.2325 B.114 C.11 1.2326 B.115 C.11 1.2327 B.116 C.11 1.2328 B.117 C.111.2329 B.118 C.11 1.2330 B.119 C.11 1.2331 B.120 C.11 1.2332 B.121 C.111.2333 B.122 C.11 1.2334 B.123 C.11 1.2335 B.124 C.11 1.2336 B.125 C.111.2337 B.126 C.11 1.2338 B.127 C.11 1.2339 B.128 C.11 1.2340 B.129 C.111.2341 B.130 C.11 1.2342 B.131 C.11 1.2343 B.132 C.11 1.2344 B.133 C.111.2345 B.134 C.11 1.2346 B.135 C.11 1.2347 B.136 C.11 1.2348 B.137 C.111.2349 B.138 C.11 1.2350 B.139 C.11 1.2351 B.140 C.11 1.2352 B.141 C.111.2353 B.142 C.11 1.2354 B.143 C.11 1.2355 B.144 C.11 1.2356 B.145 C.111.2357 B.146 C.11 1.2358 B.147 C.11 1.2359 B.148 C.11 1.2360 B.149 C.111.2361 B.150 C.11 1.2362 B.151 C.11 1.2363 B.152 C.11 1.2364 B.153 C.111.2365 B.154 C.11 1.2366 B.155 C.11 1.2367 B.156 C.11 1.2368 B.157 C.111.2369 B.158 C.11 1.2370 B.159 C.11 1.2371 B.160 C.11 1.2372 B.161 C.111.2373 B.162 C.11 1.2374 B.163 C.11 1.2375 B.164 C.11 1.2376 B.165 C.111.2377 B.166 C.11 1.2378 B.167 C.11 1.2379 B.168 C.11 1.2380 B.169 C.111.2381 B.170 C.11 1.2382 B.171 C.11 1.2383 B.172 C.11 1.2384 B.173 C.111.2385 B.174 C.11 1.2386 B.175 C.11 1.2387 B.176 C.11 1.2388 B.177 C.111.2389 B.178 C.11 1.2390 B.179 C.11 1.2391 B.180 C.11 1.2392 B.181 C.111.2393 B.182 C.11 1.2394 B.183 C.11 1.2395 B.184 C.11 1.2396 B.185 C.111.2397 B.186 C.11 1.2398 B.187 C.11 1.2399 B.188 C.11 1.2400 B.189 C.111.2401 B.190 C.11 1.2402 B.191 C.11 1.2403 B.192 C.11 1.2404 B.193 C.111.2405 B.194 C.11 1.2406 B.195 C.11 1.2407 B.196 C.11 1.2408 B.197 C.111.2409 B.198 C.11 1.2410 B.199 C.11 1.2411 B.200 C.11 1.2412 B.201 C.111.2413 B.1 C.12 1.2414 B.2 C.12 1.2415 B.3 C.12 1.2416 B.4 C.12 1.2417B.5 C.12 1.2418 B.6 C.12 1.2419 B.7 C.12 1.2420 B.8 C.12 1.2421 B.9 C.121.2422 B.10 C.12 1.2423 B.11 C.12 1.2424 B.12 C.12 1.2425 B.13 C.121.2426 B.14 C.12 1.2427 B.15 C.12 1.2428 B.16 C.12 1.2429 B.17 C.121.2430 B.18 C.12 1.2431 B.19 C.12 1.2432 B.20 C.12 1.2433 B.21 C.121.2434 B.22 C.12 1.2435 B.23 C.12 1.2436 B.24 C.12 1.2437 B.25 C.121.2438 B.26 C.12 1.2439 B.27 C.12 1.2440 B.28 C.12 1.2441 B.29 C.121.2442 B.30 C.12 1.2443 B.31 C.12 1.2444 B.32 C.12 1.2445 B.33 C.121.2446 B.34 C.12 1.2447 B.35 C.12 1.2448 B.36 C.12 1.2449 B.37 C.121.2450 B.38 C.12 1.2451 B.39 C.12 1.2452 B.40 C.12 1.2453 B.41 C.121.2454 B.42 C.12 1.2455 B.43 C.12 1.2456 B.44 C.12 1.2457 B.45 C.121.2458 B.46 C.12 1.2459 B.47 C.12 1.2460 B.48 C.12 1.2461 B.49 C.121.2462 B.50 C.12 1.2463 B.51 C.12 1.2464 B.52 C.12 1.2465 B.53 C.121.2466 B.54 C.12 1.2467 B.55 C.12 1.2468 B.56 C.12 1.2469 B.57 C.121.2470 B.58. C.12 1.2471 B.59 C.12 1.2472 B.60 C.12 1.2473 B.61 C.121.2474 B.62 C.12 1.2475 B.63 C.12 1.2476 B.64 C.12 1.2477 B.65 C.121.2478 B.66 C.12 1.2479 B.67 C.12 1.2480 B.68 C.12 1.2481 B.69 C.121.2482 B.70 C.12 1.2483 B.71 C.12 1.2484 B.72 C.12 1.2485 B.73 C.121.2486 B.74 C.12 1.2487 B.75 C.12 1.2488 B.76 C.12 1.2489 B.77 C.121.2490 B.78 C.12 1.2491 B.79 C.12 1.2492 B.80 C.12 1.2493 B.81 C.121.2494 B.82 C.12 1.2495 B.83 C.12 1.2496 B.84 C.12 1.2497 B.85 C.121.2498 B.86 C.12 1.2499 B.87 C.12 1.2500 B.88 C.12 1.2501 B.89 C.121.2502 B.90 C.12 1.2503 B.91 C.12 1.2504 B.92 C.12 1.2505 B.93 C.121.2506 B.94 C.12 1.2507 B.95 C.12 1.2508 B.96 C.12 1.2509 B.97 C.121.2510 B.98 C.12 1.2511 B.99 C.12 1.2512 B.100 C.12 1.2513 B.101 C.121.2514 B.102 C.12 1.2515 B.103 C.12 1.2516 B.104 C.12 1.2517 B.105 C.121.2518 B.106 C.12 1.2519 B.107 C.12 1.2520 B.108 C.12 1.2521 B.109 C.121.2522 B.110 C.12 1.2523 B.111 C.12 1.2524 B.112 C.12 1.2525 B.113 C.121.2526 B.114 C.12 1.2527 B.115 C.12 1.2528 B.116 C.12 1.2529 B.117 C.121.2530 B.118 C.12 1.2531 B.119 C.12 1.2532 B.120 C.12 1.2533 B.121 C.121.2534 B.122 C.12 1.2535 B.123 C.12 1.2536 B.124 C.12 1.2537 B.125 C.121.2538 B.126 C.12 1.2539 B.127 C.12 1.2540 B.128 C.12 1.2541 B.129 C.121.2542 B.130 C.12 1.2543 B.131 C.12 1.2544 B.132 C.12 1.2545 B.133 C.121.2546 B.134 C.12 1.2547 B.135 C.12 1.2548 B.136 C.12 1.2549 B.137 C.121.2550 B.138 C.12 1.2551 B.139 C.12 1.2552 B.140 C.12 1.2553 B.141 C.121.2554 B.142 C.12 1.2555 B.143 C.12 1.2556 B.144 C.12 1.2557 B.145 C.121.2558 B.146 C.12 1.2559 B.147 C.12 1.2560 B.148 C.12 1.2561 B.149 C.121.2562 B.150 C.12 1.2563 B.151 C.12 1.2564 B.152 C.12 1.2565 B.153 C.121.2566 B.154 C.12 1.2567 B.155 C.12 1.2568 B.156 C.12 1.2569 B.157 C.121.2570 B.158 C.12 1.2571 B.159 C.12 1.2572 B.160 C.12 1.2573 B.161 C.121.2574 B.162 C.12 1.2575 B.163 C.12 1.2576 B.164 C.12 1.2577 B.165 C.121.2578 B.166 C.12 1.2579 B.167 C.12 1.2580 B.168 C.12 1.2581 B.169 C.121.2582 B.170 C.12 1.2583 B.171 C.12 1.2584 B.172 C.12 1.2585 B.173 C.121.2586 B.174 C.12 1.2587 B.175 C.12 1.2588 B.176 C.12 1.2589 B.177 C.121.2590 B.178 C.12 1.2591 B.179 C.12 1.2592 B.180 C.12 1.2593 B.181 C.121.2594 B.182 C.12 1.2595 B.183 C.12 1.2596 B.184 C.12 1.2597 B.185 C.121.2598 B.186 C.12 1.2599 B.187 C.12 1.2600 B.188 C.12 1.2601 B.189 C.121.2602 B.190 C.12 1.2603 B.191 C.12 1.2604 B.192 C.12 1.2605 B.193 C.121.2606 B.194 C.12 1.2607 B.195 C.12 1.2608 B.196 C.12 1.2609 B.197 C.121.2610 B.198 C.12 1.2611 B.199 C.12 1.2612 B.200 C.12 1.2613 B.201 C.121.2614 B.1 C.13 1.2615 B.2 C.13 1.2616 B.3 C.13 1.2617 B.4 C.13 1.2618B.5 C.13 1.2619 B.6 C.13 1.2620 B.7 C.13 1.2621 B.8 C.13 1.2622 B.9 C.131.2623 B.10 C.13 1.2624 B.11 C.13 1.2625 B.12 C.13 1.2626 B.13 C.131.2627 B.14 C.13 1.2628 B.15 C.13 1.2629 B.16 C.13 1.2630 B.17 C.131.2631 B.18 C.13 1.2632 B.19 C.13 1.2633 B.20 C.13 1.2634 B.21 C.131.2635 B.22 C.13 1.2636 B.23 C.13 1.2637 B.24 C.13 1.2638 B.25 C.131.2639 B.26 C.13 1.2640 B.27 C.13 1.2641 B.28 C.13 1.2642 B.29 C.131.2643 B.30 C.13 1.2644 B.31 C.13 1.2645 B.32 C.13 1.2646 B.33 C.131.2647 B.34 C.13 1.2648 B.35 C.13 1.2649 B.36 C.13 1.2650 B.37 C.131.2651 B.38 C.13 1.2652 B.39 C.13 1.2653 B.40 C.13 1.2654 B.41 C.131.2655 B.42 C.13 1.2656 B.43 C.13 1.2657 B.44 C.13 1.2658 B.45 C.131.2659 B.46 C.13 1.2660 B.47 C.13 1.2661 B.48 C.13 1.2662 B.49 C.131.2663 B.50 C.13 1.2664 B.51 C.13 1.2665 B.52 C.13 1.2666 B.53 C.131.2667 B.54 C.13 1.2668 B.55 C.13 1.2669 B.56 C.13 1.2670 B.57 C.131.2671 B.58. C.13 1.2672 B.59 C.13 1.2673 B.60 C.13 1.2674 B.61 C.131.2675 B.62 C.13 1.2676 B.63 C.13 1.2677 B.64 C.13 1.2678 B.65 C.131.2679 B.66 C.13 1.2680 B.67 C.13 1.2681 B.68 C.13 1.2682 B.69 C.131.2683 B.70 C.13 1.2684 B.71 C.13 1.2685 B.72 C.13 1.2686 B.73 C.131.2687 B.74 C.13 1.2688 B.75 C.13 1.2689 B.76 C.13 1.2690 B.77 C.131.2691 B.78 C.13 1.2692 B.79 C.13 1.2693 B.80 C.13 1.2694 B.81 C.131.2695 B.82 C.13 1.2696 B.83 C.13 1.2697 B.84 C.13 1.2698 B.85 C.131.2699 B.86 C.13 1.2700 B.87 C.13 1.2701 B.88 C.13 1.2702 B.89 C.131.2703 B.90 C.13 1.2704 B.91 C.13 1.2705 B.92 C.13 1.2706 B.93 C.131.2707 B.94 C.13 1.2708 B.95 C.13 1.2709 B.96 C.13 1.2710 B.97 C.131.2711 B.98 C.13 1.2712 B.99 C.13 1.2713 B.100 C.13 1.2714 B.101 C.131.2715 B.102 C.13 1.2716 B.103 C.13 1.2717 B.104 C.13 1.2718 B.105 C.131.2719 B.106 C.13 1.2720 B.107 C.13 1.2721 B.108 C.13 1.2722 B.109 C.131.2723 B.110 C.13 1.2724 B.111 C.13 1.2725 B.112 C.13 1.2726 B.113 C.131.2727 B.114 C.13 1.2728 B.115 C.13 1.2729 B.116 C.13 1.2730 B.117 C.131.2731 B.118 C.13 1.2732 B.119 C.13 1.2733 B.120 C.13 1.2734 B.121 C.131.2735 B.122 C.13 1.2736 B.123 C.13 1.2737 B.124 C.13 1.2738 B.125 C.131.2739 B.126 C.13 1.2740 B.127 C.13 1.2741 B.128 C.13 1.2742 B.129 C.131.2743 B.130 C.13 1.2744 B.131 C.13 1.2745 B.132 C.13 1.2746 B.133 C.131.2747 B.134 C.13 1.2748 B.135 C.13 1.2749 B.136 C.13 1.2750 B.137 C.131.2751 B.138 C.13 1.2752 B.139 C.13 1.2753 B.140 C.13 1.2754 B.141 C.131.2755 B.142 C.13 1.2756 B.143 C.13 1.2757 B.144 C.13 1.2758 B.145 C.131.2759 B.146 C.13 1.2760 B.147 C.13 1.2761 B.148 C.13 1.2762 B.149 C.131.2763 B.150 C.13 1.2764 B.151 C.13 1.2765 B.152 C.13 1.2766 B.153 C.131.2767 B.154 C.13 1.2768 B.155 C.13 1.2769 B.156 C.13 1.2770 B.157 C.131.2771 B.158 C.13 1.2772 B.159 C.13 1.2773 B.160 C.13 1.2774 B.161 C.131.2775 B.162 C.13 1.2776 B.163 C.13 1.2777 B.164 C.13 1.2778 B.165 C.131.2779 B.166 C.13 1.2780 B.167 C.13 1.2781 B.168 C.13 1.2782 B.169 C.131.2783 B.170 C.13 1.2784 B.171 C.13 1.2785 B.172 C.13 1.2786 B.173 C.131.2787 B.174 C.13 1.2788 B.175 C.13 1.2789 B.176 C.13 1.2790 B.177 C.131.2791 B.178 C.13 1.2792 B.179 C.13 1.2793 B.180 C.13 1.2794 B.181 C.131.2795 B.182 C.13 1.2796 B.183 C.13 1.2797 B.184 C.13 1.2798 B.185 C.131.2799 B.186 C.13 1.2800 B.187 C.13 1.2801 B.188 C.13 1.2802 B.189 C.131.2803 B.190 C.13 1.2804 B.191 C.13 1.2805 B.192 C.13 1.2806 B.193 C.131.2807 B.194 C.13 1.2808 B.195 C.13 1.2809 B.196 C.13 1.2810 B.197 C.131.2811 B.198 C.13 1.2812 B.199 C.13 1.2813 B.200 C.13 1.2814 B.201 C.131.2815 B.1 C.14 1.2816 B.2 C.14 1.2817 B.3 C.14 1.2818 B.4 C.14 1.2819B.5 C.14 1.2820 B.6 C.14 1.2821 B.7 C.14 1.2822 B.8 C.14 1.2823 B.9 C.141.2824 B.10 C.14 1.2825 B.11 C.14 1.2826 B.12 C.14 1.2827 B.13 C.141.2828 B.14 C.14 1.2829 B.15 C.14 1.2830 B.16 C.14 1.2831 B.17 C.141.2832 B.18 C.14 1.2833 B.19 C.14 1.2834 B.20 C.14 1.2835 B.21 C.141.2836 B.22 C.14 1.2837 B.23 C.14 1.2838 B.24 C.14 1.2839 B.25 C.141.2840 B.26 C.14 1.2841 B.27 C.14 1.2842 B.28 C.14 1.2843 B.29 C.141.2844 B.30 C.14 1.2845 B.31 C.14 1.2846 B.32 C.14 1.2847 B.33 C.141.2848 B.34 C.14 1.2849 B.35 C.14 1.2850 B.36 C.14 1.2851 B.37 C.141.2852 B.38 C.14 1.2853 B.39 C.14 1.2854 B.40 C.14 1.2855 B.41 C.141.2856 B.42 C.14 1.2857 B.43 C.14 1.2858 B.44 C.14 1.2859 B.45 C.141.2860 B.46 C.14 1.2861 B.47 C.14 1.2862 B.48 C.14 1.2863 B.49 C.141.2864 B.50 C.14 1.2865 B.51 C.14 1.2866 B.52 C.14 1.2867 B.53 C.141.2868 B.54 C.14 1.2869 B.55 C.14 1.2870 B.56 C.14 1.2871 B.57 C.141.2872 B.58. C.14 1.2873 B.59 C.14 1.2874 B.60 C.14 1.2875 B.61 C.141.2876 B.62 C.14 1.2877 B.63 C.14 1.2878 B.64 C.14 1.2879 B.65 C.141.2880 B.66 C.14 1.2881 B.67 C.14 1.2882 B.68 C.14 1.2883 B.69 C.141.2884 B.70 C.14 1.2885 B.71 C.14 1.2886 B.72 C.14 1.2887 B.73 C.141.2888 B.74 C.14 1.2889 B.75 C.14 1.2890 B.76 C.14 1.2891 B.77 C.141.2892 B.78 C.14 1.2893 B.79 C.14 1.2894 B.80 C.14 1.2895 B.81 C.141.2896 B.82 C.14 1.2897 B.83 C.14 1.2898 B.84 C.14 1.2899 B.85 C.141.2900 B.86 C.14 1.2901 B.87 C.14 1.2902 B.88 C.14 1.2903 B.89 C.141.2904 B.90 C.14 1.2905 B.91 C.14 1.2906 B.92 C.14 1.2907 B.93 C.141.2908 B.94 C.14 1.2909 B.95 C.14 1.2910 B.96 C.14 1.2911 B.97 C.141.2912 B.98 C.14 1.2913 B.99 C.14 1.2914 B.100 C.14 1.2915 B.101 C.141.2916 B.102 C.14 1.2917 B.103 C.14 1.2918 B.104 C.14 1.2919 B.105 C.141.2920 B.106 C.14 1.2921 B.107 C.14 1.2922 B.108 C.14 1.2923 B.109 C.141.2924 B.110 C.14 1.2925 B.111 C.14 1.2926 B.112 C.14 1.2927 B.113 C.141.2928 B.114 C.14 1.2929 B.115 C.14 1.2930 B.116 C.14 1.2931 B.117 C.141.2932 B.118 C.14 1.2933 B.119 C.14 1.2934 B.120 C.14 1.2935 B.121 C.141.2936 B.122 C.14 1.2937 B.123 C.14 1.2938 B.124 C.14 1.2939 B.125 C.141.2940 B.126 C.14 1.2941 B.127 C.14 1.2942 B.128 C.14 1.2943 B.129 C.141.2944 B.130 C.14 1.2945 B.131 C.14 1.2946 B.132 C.14 1.2947 B.133 C.141.2948 B.134 C.14 1.2949 B.135 C.14 1.2950 B.136 C.14 1.2951 B.137 C.141.2952 B.138 C.14 1.2953 B.139 C.14 1.2954 B.140 C.14 1.2955 B.141 C.141.2956 B.142 C.14 1.2957 B.143 C.14 1.2958 B.144 C.14 1.2959 B.145 C.141.2960 B.146 C.14 1.2961 B.147 C.14 1.2962 B.148 C.14 1.2963 B.149 C.141.2964 B.150 C.14 1.2965 B.151 C.14 1.2966 B.152 C.14 1.2967 B.153 C.141.2968 B.154 C.14 1.2969 B.155 C.14 1.2970 B.156 C.14 1.2971 B.157 C.141.2972 B.158 C.14 1.2973 B.159 C.14 1.2974 B.160 C.14 1.2975 B.161 C.141.2976 B.162 C.14 1.2977 B.163 C.14 1.2978 B.164 C.14 1.2979 B.165 C.141.2980 B.166 C.14 1.2981 B.167 C.14 1.2982 B.168 C.14 1.2983 B.169 C.141.2984 B.170 C.14 1.2985 B.171 C.14 1.2986 B.172 C.14 1.2987 B.173 C.141.2988 B.174 C.14 1.2989 B.175 C.14 1.2990 B.176 C.14 1.2991 B.177 C.141.2992 B.178 C.14 1.2993 B.179 C.14 1.2994 B.180 C.14 1.2995 B.181 C.141.2996 B.182 C.14 1.2997 B.183 C.14 1.2998 B.184 C.14 1.2999 B.185 C.141.3000 B.186 C.14 1.3001 B.187 C.14 1.3002 B.188 C.14 1.3003 B.189 C.141.3004 B.190 C.14 1.3005 B.191 C.14 1.3006 B.192 C.14 1.3007 B.193 C.141.3008 B.194 C.14 1.3009 B.195 C.14 1.3010 B.196 C.14 1.3011 B.197 C.141.3012 B.198 C.14 1.3013 B.199 C.14 1.3014 B.200 C.14 1.3015 B.201 C.141.3016 B.1 C.15 1.3017 B.2 C.15 1.3018 B.3 C.15 1.3019 B.4 C.15 1.3020B.5 C.15 1.3021 B.6 C.15 1.3022 B.7 C.15 1.3023 B.8 C.15 1.3024 B.9 C.151.3025 B.10 C.15 1.3026 B.11 C.15 1.3027 B.12 C.15 1.3028 B.13 C.151.3029 B.14 C.15 1.3030 B.15 C.15 1.3031 B.16 C.15 1.3032 B.17 C.151.3033 B.18 C.15 1.3034 B.19 C.15 1.3035 B.20 C.15 1.3036 B.21 C.151.3037 B.22 C.15 1.3038 B.23 C.15 1.3039 B.24 C.15 1.3040 B.25 C.151.3041 B.26 C.15 1.3042 B.27 C.15 1.3043 B.28 C.15 1.3044 B.29 C.151.3045 B.30 C.15 1.3046 B.31 C.15 1.3047 B.32 C.15 1.3048 B.33 C.151.3049 B.34 C.15 1.3050 B.35 C.15 1.3051 B.36 C.15 1.3052 B.37 C.151.3053 B.38 C.15 1.3054 B.39 C.15 1.3055 B.40 C.15 1.3056 B.41 C.151.3057 B.42 C.15 1.3058 B.43 C.15 1.3059 B.44 C.15 1.3060 B.45 C.151.3061 B.46 C.15 1.3062 B.47 C.15 1.3063 B.48 C.15 1.3064 B.49 C.151.3065 B.50 C.15 1.3066 B.51 C.15 1.3067 B.52 C.15 1.3068 B.53 C.151.3069 B.54 C.15 1.3070 B.55 C.15 1.3071 B.56 C.15 1.3072 B.57 C.151.3073 B.58. C.15 1.3074 B.59 C.15 1.3075 B.60 C.15 1.3076 B.61 C.151.3077 B.62 C.15 1.3078 B.63 C.15 1.3079 B.64 C.15 1.3080 B.65 C.151.3081 B.66 C.15 1.3082 B.67 C.15 1.3083 B.68 C.15 1.3084 B.69 C.151.3085 B.70 C.15 1.3086 B.71 C.15 1.3087 B.72 C.15 1.3088 B.73 C.151.3089 B.74 C.15 1.3090 B.75 C.15 1.3091 B.76 C.15 1.3092 B.77 C.151.3093 B.78 C.15 1.3094 B.79 C.15 1.3095 B.80 C.15 1.3096 B.81 C.151.3097 B.82 C.15 1.3098 B.83 C.15 1.3099 B.84 C.15 1.3100 B.85 C.151.3101 B.86 C.15 1.3102 B.87 C.15 1.3103 B.88 C.15 1.3104 B.89 C.151.3105 B.90 C.15 1.3106 B.91 C.15 1.3107 B.92 C.15 1.3108 B.93 C.151.3109 B.94 C.15 1.3110 B.95 C.15 1.3111 B.96 C.15 1.3112 B.97 C.151.3113 B.98 C.15 1.3114 B.99 C.15 1.3115 B.100 C.15 1.3116 B.101 C.151.3117 B.102 C.15 1.3118 B.103 C.15 1.3119 B.104 C.15 1.3120 B.105 C.151.3121 B.106 C.15 1.3122 B.107 C.15 1.3123 B.108 C.15 1.3124 B.109 C.151.3125 B.110 C.15 1.3126 B.111 C.15 1.3127 B.112 C.15 1.3128 B.113 C.151.3129 B.114 C.15 1.3130 B.115 C.15 1.3131 B.116 C.15 1.3132 B.117 C.151.3133 B.118 C.15 1.3134 B.119 C.15 1.3135 B.120 C.15 1.3136 B.121 C.151.3137 B.122 C.15 1.3138 B.123 C.15 1.3139 B.124 C.15 1.3140 B.125 C.151.3141 B.126 C.15 1.3142 B.127 C.15 1.3143 B.128 C.15 1.3144 B.129 C.151.3145 B.130 C.15 1.3146 B.131 C.15 1.3147 B.132 C.15 1.3148 B.133 C.151.3149 B.134 C.15 1.3150 B.135 C.15 1.3151 B.136 C.15 1.3152 B.137 C.151.3153 B.138 C.15 1.3154 B.139 C.15 1.3155 B.140 C.15 1.3156 B.141 C.151.3157 B.142 C.15 1.3158 B.143 C.15 1.3159 B.144 C.15 1.3160 B.145 C.151.3161 B.146 C.15 1.3162 B.147 C.15 1.3163 B.148 C.15 1.3164 B.149 C.151.3165 B.150 C.15 1.3166 B.151 C.15 1.3167 B.152 C.15 1.3168 B.153 C.151.3169 B.154 C.15 1.3170 B.155 C.15 1.3171 B.156 C.15 1.3172 B.157 C.151.3173 B.158 C.15 1.3174 B.159 C.15 1.3175 B.160 C.15 1.3176 B.161 C.151.3177 B.162 C.15 1.3178 B.163 C.15 1.3179 B.164 C.15 1.3180 B.165 C.151.3181 B.166 C.15 1.3182 B.167 C.15 1.3183 B.168 C.15 1.3184 B.169 C.151.3185 B.170 C.15 1.3186 B.171 C.15 1.3187 B.172 C.15 1.3188 B.173 C.151.3189 B.174 C.15 1.3190 B.175 C.15 1.3191 B.176 C.15 1.3192 B.177 C.151.3193 B.178 C.15 1.3194 B.179 C.15 1.3195 B.180 C.15 1.3196 B.181 C.151.3197 B.182 C.15 1.3198 B.183 C.15 1.3199 B.184 C.15 1.3200 B.185 C.151.3201 B.186 C.15 1.3202 B.187 C.15 1.3203 B.188 C.15 1.3204 B.189 C.151.3205 B.190 C.15 1.3206 B.191 C.15 1.3207 B.192 C.15 1.3208 B.193 C.151.3209 B.194 C.15 1.3210 B.195 C.15 1.3211 B.196 C.15 1.3212 B.197 C.151.3213 B.198 C.15 1.3214 B.199 C.15 1.3215 B.200 C.15 1.3216 B.201 C.151.3217 B.1 C.16 1.3218 B.2 C.16 1.3219 B.3 C.16 1.3220 B.4 C.16 1.3221B.5 C.16 1.3222 B.6 C.16 1.3223 B.7 C.16 1.3224 B.8 C.16 1.3225 B.9 C.161.3226 B.10 C.16 1.3227 B.11 C.16 1.3228 B.12 C.16 1.3229 B.13 C.161.3230 B.14 C.16 1.3231 B.15 C.16 1.3232 B.16 C.16 1.3233 B.17 C.161.3234 B.18 C.16 1.3235 B.19 C.16 1.3236 B.20 C.16 1.3237 B.21 C.161.3238 B.22 C.16 1.3239 B.23 C.16 1.3240 B.24 C.16 1.3241 B.25 C.161.3242 B.26 C.16 1.3243 B.27 C.16 1.3244 B.28 C.16 1.3245 B.29 C.161.3246 B.30 C.16 1.3247 B.31 C.16 1.3248 B.32 C.16 1.3249 B.33 C.161.3250 B.34 C.16 1.3251 B.35 C.16 1.3252 B.36 C.16 1.3253 B.37 C.161.3254 B.38 C.16 1.3255 B.39 C.16 1.3256 B.40 C.16 1.3257 B.41 C.161.3258 B.42 C.16 1.3259 B.43 C.16 1.3260 B.44 C.16 1.3261 B.45 C.161.3262 B.46 C.16 1.3263 B.47 C.16 1.3264 B.48 C.16 1.3265 B.49 C.161.3266 B.50 C.16 1.3267 B.51 C.16 1.3268 B.52 C.16 1.3269 B.53 C.161.3270 B.54 C.16 1.3271 B.55 C.16 1.3272 B.56 C.16 1.3273 B.57 C.161.3274 B.58. C.16 1.3275 B.59 C.16 1.3276 B.60 C.16 1.3277 B.61 C.161.3278 B.62 C.16 1.3279 B.63 C.16 1.3280 B.64 C.16 1.3281 B.65 C.161.3282 B.66 C.16 1.3283 B.67 C.16 1.3284 B.68 C.16 1.3285 B.69 C.161.3286 B.70 C.16 1.3287 B.71 C.16 1.3288 B.72 C.16 1.3289 B.73 C.161.3290 B.74 C.16 1.3291 B.75 C.16 1.3292 B.76 C.16 1.3293 B.77 C.161.3294 B.78 C.16 1.3295 B.79 C.16 1.3296 B.80 C.16 1.3297 B.81 C.161.3298 B.82 C.16 1.3299 B.83 C.16 1.3300 B.84 C.16 1.3301 B.85 C.161.3302 B.86 C.16 1.3303 B.87 C.16 1.3304 B.88 C.16 1.3305 B.89 C.161.3306 B.90 C.16 1.3307 B.91 C.16 1.3308 B.92 C.16 1.3309 B.93 C.161.3310 B.94 C.16 1.3311 B.95 C.16 1.3312 B.96 C.16 1.3313 B.97 C.161.3314 B.98 C.16 1.3315 B.99 C.16 1.3316 B.100 C.16 1.3317 B.101 C.161.3318 B.102 C.16 1.3319 B.103 C.16 1.3320 B.104 C.16 1.3321 B.105 C.161.3322 B.106 C.16 1.3323 B.107 C.16 1.3324 B.108 C.16 1.3325 B.109 C.161.3326 B.110 C.16 1.3327 B.111 C.16 1.3328 B.112 C.16 1.3329 B.113 C.161.3330 B.114 C.16 1.3331 B.115 C.16 1.3332 B.116 C.16 1.3333 B.117 C.161.3334 B.118 C.16 1.3335 B.119 C.16 1.3336 B.120 C.16 1.3337 B.121 C.161.3338 B.122 C.16 1.3339 B.123 C.16 1.3340 B.124 C.16 1.3341 B.125 C.161.3342 B.126 C.16 1.3343 B.127 C.16 1.3344 B.128 C.16 1.3345 B.129 C.161.3346 B.130 C.16 1.3347 B.131 C.16 1.3348 B.132 C.16 1.3349 B.133 C.161.3350 B.134 C.16 1.3351 B.135 C.16 1.3352 B.136 C.16 1.3353 B.137 C.161.3354 B.138 C.16 1.3355 B.139 C.16 1.3356 B.140 C.16 1.3357 B.141 C.161.3358 B.142 C.16 1.3359 B.143 C.16 1.3360 B.144 C.16 1.3361 B.145 C.161.3362 B.146 C.16 1.3363 B.147 C.16 1.3364 B.148 C.16 1.3365 B.149 C.161.3366 B.150 C.16 1.3367 B.151 C.16 1.3368 B.152 C.16 1.3369 B.153 C.161.3370 B.154 C.16 1.3371 B.155 C.16 1.3372 B.156 C.16 1.3373 B.157 C.161.3374 B.158 C.16 1.3375 B.159 C.16 1.3376 B.160 C.16 1.3377 B.161 C.161.3378 B.162 C.16 1.3379 B.163 C.16 1.3380 B.164 C.16 1.3381 B.165 C.161.3382 B.166 C.16 1.3383 B.167 C.16 1.3384 B.168 C.16 1.3385 B.169 C.161.3386 B.170 C.16 1.3387 B.171 C.16 1.3388 B.172 C.16 1.3389 B.173 C.161.3390 B.174 C.16 1.3391 B.175 C.16 1.3392 B.176 C.16 1.3393 B.177 C.161.3394 B.178 C.16 1.3395 B.179 C.16 1.3396 B.180 C.16 1.3397 B.181 C.161.3398 B.182 C.16 1.3399 B.183 C.16 1.3400 B.184 C.16 1.3401 B.185 C.161.3402 B.186 C.16 1.3403 B.187 C.16 1.3404 B.188 C.16 1.3405 B.189 C.161.3406 B.190 C.16 1.3407 B.191 C.16 1.3408 B.192 C.16 1.3409 B.193 C.161.3410 B.194 C.16 1.3411 B.195 C.16 1.3412 B.196 C.16 1.3413 B.197 C.161.3414 B.198 C.16 1.3415 B.199 C.16 1.3416 B.200 C.16 1.3417 B.201 C.161.3418 B.1 C.17 1.3419 B.2 C.17 1.3420 B.3 C.17 1.3421 B.4 C.17 1.3422B.5 C.17 1.3423 B.6 C.17 1.3424 B.7 C.17 1.3425 B.8 C.17 1.3426 B.9 C.171.3427 B.10 C.17 1.3428 B.11 C.17 1.3429 B.12 C.17 1.3430 B.13 C.171.3431 B.14 C.17 1.3432 B.15 C.17 1.3433 B.16 C.17 1.3434 B.17 C.171.3435 B.18 C.17 1.3436 B.19 C.17 1.3437 B.20 C.17 1.3438 B.21 C.171.3439 B.22 C.17 1.3440 B.23 C.17 1.3441 B.24 C.17 1.3442 B.25 C.171.3443 B.26 C.17 1.3444 B.27 C.17 1.3445 B.28 C.17 1.3446 B.29 C.171.3447 B.30 C.17 1.3448 B.31 C.17 1.3449 B.32 C.17 1.3450 B.33 C.171.3451 B.34 C.17 1.3452 B.35 C.17 1.3453 B.36 C.17 1.3454 B.37 C.171.3455 B.38 C.17 1.3456 B.39 C.17 1.3457 B.40 C.17 1.3458 B.41 C.171.3459 B.42 C.17 1.3460 B.43 C.17 1.3461 B.44 C.17 1.3462 B.45 C.171.3463 B.46 C.17 1.3464 B.47 C.17 1.3465 B.48 C.17 1.3466 B.49 C.171.3467 B.50 C.17 1.3468 B.51 C.17 1.3469 B.52 C.17 1.3470 B.53 C.171.3471 B.54 C.17 1.3472 B.55 C.17 1.3473 B.56 C.17 1.3474 B.57 C.171.3475 B.58. C.17 1.3476 B.59 C.17 1.3477 B.60 C.17 1.3478 B.61 C.171.3479 B.62 C.17 1.3480 B.63 C.17 1.3481 B.64 C.17 1.3482 B.65 C.171.3483 B.66 C.17 1.3484 B.67 C.17 1.3485 B.68 C.17 1.3486 B.69 C.171.3487 B.70 C.17 1.3488 B.71 C.17 1.3489 B.72 C.17 1.3490 B.73 C.171.3491 B.74 C.17 1.3492 B.75 C.17 1.3493 B.76 C.17 1.3494 B.77 C.171.3495 B.78 C.17 1.3496 B.79 C.17 1.3497 B.80 C.17 1.3498 B.81 C.171.3499 B.82 C.17 1.3500 B.83 C.17 1.3501 B.84 C.17 1.3502 B.85 C.171.3503 B.86 C.17 1.3504 B.87 C.17 1.3505 B.88 C.17 1.3506 B.89 C.171.3507 B.90 C.17 1.3508 B.91 C.17 1.3509 B.92 C.17 1.3510 B.93 C.171.3511 B.94 C.17 1.3512 B.95 C.17 1.3513 B.96 C.17 1.3514 B.97 C.171.3515 B.98 C.17 1.3516 B.99 C.17 1.3517 B.100 C.17 1.3518 B.101 C.171.3519 B.102 C.17 1.3520 B.103 C.17 1.3521 B.104 C.17 1.3522 B.105 C.171.3523 B.106 C.17 1.3524 B.107 C.17 1.3525 B.108 C.17 1.3526 B.109 C.171.3527 B.110 C.17 1.3528 B.111 C.17 1.3529 B.112 C.17 1.3530 B.113 C.171.3531 B.114 C.17 1.3532 B.115 C.17 1.3533 B.116 C.17 1.3534 B.117 C.171.3535 B.118 C.17 1.3536 B.119 C.17 1.3537 B.120 C.17 1.3538 B.121 C.171.3539 B.122 C.17 1.3540 B.123 C.17 1.3541 B.124 C.17 1.3542 B.125 C.171.3543 B.126 C.17 1.3544 B.127 C.17 1.3545 B.128 C.17 1.3546 B.129 C.171.3547 B.130 C.17 1.3548 B.131 C.17 1.3549 B.132 C.17 1.3550 B.133 C.171.3551 B.134 C.17 1.3552 B.135 C.17 1.3553 B.136 C.17 1.3554 B.137 C.171.3555 B.138 C.17 1.3556 B.139 C.17 1.3557 B.140 C.17 1.3558 B.141 C.171.3559 B.142 C.17 1.3560 B.143 C.17 1.3561 B.144 C.17 1.3562 B.145 C.171.3563 B.146 C.17 1.3564 B.147 C.17 1.3565 B.148 C.17 1.3566 B.149 C.171.3567 B.150 C.17 1.3568 B.151 C.17 1.3569 B.152 C.17 1.3570 B.153 C.171.3571 B.154 C.17 1.3572 B.155 C.17 1.3573 B.156 C.17 1.3574 B.157 C.171.3575 B.158 C.17 1.3576 B.159 C.17 1.3577 B.160 C.17 1.3578 B.161 C.171.3579 B.162 C.17 1.3580 B.163 C.17 1.3581 B.164 C.17 1.3582 B.165 C.171.3583 B.166 C.17 1.3584 B.167 C.17 1.3585 B.168 C.17 1.3586 B.169 C.171.3587 B.170 C.17 1.3588 B.171 C.17 1.3589 B.172 C.17 1.3590 B.173 C.171.3591 B.174 C.17 1.3592 B.175 C.17 1.3593 B.176 C.17 1.3594 B.177 C.171.3595 B.178 C.17 1.3596 B.179 C.17 1.3597 B.180 C.17 1.3598 B.181 C.171.3599 B.182 C.17 1.3600 B.183 C.17 1.3601 B.184 C.17 1.3602 B.185 C.171.3603 B.186 C.17 1.3604 B.187 C.17 1.3605 B.188 C.17 1.3606 B.189 C.171.3607 B.190 C.17 1.3608 B.191 C.17 1.3609 B.192 C.17 1.3610 B.193 C.171.3611 B.194 C.17 1.3612 B.195 C.17 1.3613 B.196 C.17 1.3614 B.197 C.171.3615 B.198 C.17 1.3616 B.199 C.17 1.3617 B.200 C.17 1.3618 B.201 C.171.3619 — C.1 1.3620 — C.2 1.3621 — C.3 1.3622 — C.4 1.3623 — C.5 1.3624— C.6 1.3625 — C.7 1.3626 — C.8 1.3627 — C.9 1.3628 — C.10 1.3629 — C.111.3630 — C.12 1.3631 — C.13 1.3632 — C.14 1.3633 — C.15 1.3634 — C.161.3635 — C.17

It may furthermore be beneficial to apply the benzoxaborole compounds offormula (I) alone or in combination with other herbicides, or else inthe form of a mixture with other crop protection agents, for exampletogether with agents for controlling pests or phytopathogenic fungi orbacteria. Also of interest is the miscibility with mineral saltsolutions, which are employed for treating nutritional and trace elementdeficiencies. Other additives such as non-phytotoxic oils and oilconcentrates may also be added.

The invention also relates to agrochemical compositions comprising atleast an auxiliary and at least one benzoxaborole compound of formula(I) according to the invention.

An agrochemical composition comprises a pesticidally effective amount ofa benzoxaborole compound of formula (I). The term “effective amount”denotes an amount of the composition or of the compounds I, which issufficient for controlling unwanted plants, especially for controllingunwanted plants in cultivated plants and which does not result in asubstantial damage to the treated plants. Such an amount can vary in abroad range and is dependent on various factors, such as the plants tobe controlled, the treated cultivated plant or material, the climaticconditions and the specific benzoxaborole compound of formula (I) used.

The benzoxaborole compound of formula (I), their N-oxides or salts canbe converted into customary types of agrochemical compositions, e.g.solutions, emulsions, suspensions, dusts, powders, pastes, granules,pressings, capsules, and mixtures thereof. Examples for agrochemicalcomposition types are suspensions (e.g. SC, OD, FS), emulsifiableconcentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g.CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS,DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG,MG), insecticidal articles (e.g. LN), as well as gel formulations forthe treatment of plant propagation materials such as seeds (e.g. GF).These and further agrochemical compositions types are defined in the“Catalogue of pesticide formulation types and international codingsystem”, Technical Monograph No. 2, 6^(th) Ed. May 2008, CropLifeInternational.

The agrochemical compositions are prepared in a known manner, such asdescribed by Mollet and Grubemann, Formulation technology, Wiley VCH,Weinheim, 2001; or Knowles, New developments in crop protection productformulation, Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers orfillers, surfactants, dispersants, emulsifiers, wetters, adjuvants,solubilizers, penetration enhancers, protective colloids, adhesionagents, thickeners, humectants, repellents, attractants, feedingstimulants, compatibilizers, bactericides, anti-freezing agents,anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents,such as mineral oil fractions of medium to high boiling point, e.g.kerosene, diesel oil; oils of vegetable or animal origin; aliphatic,cyclic and aromatic hydrocarbons, e.g. toluene, paraffin,tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol,propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones,e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acidesters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides,e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixturesthereof.

Suitable solid carriers or fillers are mineral earths, e.g. silicates,silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite,diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate,magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers,e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas;products of vegetable origin, e.g. cereal meal, tree bark meal, woodmeal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic,cationic, nonionic and amphoteric surfactants, block polymers,polyelectrolytes, and mixtures thereof. Such surfactants can be used asemulsifier, dispersant, solubilizer, wetter, penetration enhancer,protective colloid, or adjuvant. Examples of surfactants are listed inMcCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon'sDirectories, Glen Rock, USA, 2008 (International Ed. or North AmericanEd.).

Suitable anionic surfactants are alkali, alkaline earth or ammoniumsalts of sulfonates, sulfates, phosphates, carboxylates, and mixturesthereof. Examples of sulfonates are alkylarylsulfonates,diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates,sulfonates of fatty acids and oils, sulfonates of ethoxylatedalkylphenols, sulfonates of alkoxylated arylphenols, sulfonates ofcondensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes,sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates orsulfosuccinamates. Examples of sulfates are sulfates of fatty acids andoils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols,or of fatty acid esters. Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates, and carboxylatedalcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acidamides, amine oxides, esters, sugar-based surfactants, polymericsurfactants, and mixtures thereof. Examples of alkoxylates are compoundssuch as alcohols, alkylphenols, amines, amides, arylphenols, fatty acidsor fatty acid esters which have been alkoxylated with 1 to 50equivalents. Ethylene oxide and/or propylene oxide may be employed forthe alkoxylation, preferably ethylene oxide. Examples of N-substitutedfatty acid amides are fatty acid glucamides or fatty acid alkanolamides.Examples of esters are fatty acid esters, glycerol esters ormonoglycerides. Examples of sugar-based surfactants are sorbitans,ethoxylated sorbitans, sucrose and glucose esters oralkylpolyglucosides. Examples of polymeric surfactants are home- orcopolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactants are quaternary surfactants, for examplequaternary ammonium compounds with one or two hydrophobic groups, orsalts of long-chain primary amines. Suitable amphoteric surfactants arealkylbetains and imidazolines. Suitable block polymers are blockpolymers of the A-B or A-B-A type comprising blocks of polyethyleneoxide and polypropylene oxide, or of the A-B-C type comprising alkanol,polyethylene oxide and polypropylene oxide. Suitable polyelectrolytesare polyacids or polybases. Examples of polyacids are alkali salts ofpolyacrylic acid or polyacid comb polymers. Examples of polybases arepolyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds, which have a neglectable or even nopesticidally activity themselves, and which improve the biologicalperformance of the compound I on the target. Examples are surfactants,mineral or vegetable oils, and other auxiliaries. Further examples arelisted by Knowles, Adjuvants and additives, Agrow Reports DS256, T&FInforma UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e.g. xanthan gum,carboxymethylcellulose), inorganic clays (organically modified orunmodified), polycarboxylates, and silicates.

Suitable bactericides are bronopol and isothiazolinone derivatives suchas alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol,urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, andsalts of fatty acids.

Suitable colorants (e.g. in red, blue, or green) are pigments of lowwater solubility and water-soluble dyes. Examples are inorganiccolorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) andorganic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifiers or binders are polyvinylpyrrolidons,polyvinylacetates, polyvinyl alcohols, polyacrylates, biological orsynthetic waxes, and cellulose ethers.

Examples for agrochemical composition types and their preparation are:

-   -   i) Water-soluble concentrates (SL, LS)

10-60 wt % of an benzoxaborole compound of formula (I) according to theinvention and 5-278 wt % wetting agent (e.g. alcohol alkoxylates) aredissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad100 wt %. The active substance dissolves upon dilution with water.

-   -   ii) Dispersible concentrates (DC)

5-25 wt % of an benzoxaborole compound of formula (I) according to theinvention and 1-10 wt % dispersant (e.g. polyvinylpyrrolidone) aredissolved in organic solvent (e.g. cyclohexanone) ad 100 wt %. Dilutionwith water gives a dispersion.

-   -   iii) Emulsifiable concentrates (EC)

278-70 wt % of an benzoxaborole compound of formula (I) according to theinvention and 5-10 wt % emulsifiers (e.g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved inwater-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt %.Dilution with water gives an emulsion.

-   -   iv) Emulsions (EW, EO, ES)

5-40 wt % of an benzoxaborole compound of formula (I) according to theinvention and 1-10 wt % emulsifiers (e.g. calciumdodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in20-40 wt % water-insoluble organic solvent (e.g. aromatic hydrocarbon).This mixture is introduced into water ad 100 wt % by means of anemulsifying machine and made into a homogeneous emulsion. Dilution withwater gives an emulsion.

-   -   v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt % of an benzoxaborole compound offormula (I) according to the invention are comminuted with addition of2-10 wt % dispersants and wetting agents (e.g. sodium lignosulfonate andalcohol ethoxylate), 0.1-2 wt % thickener (e.g. xanthan gum) and waterad 100 wt % to give a fine active substance suspension. Dilution withwater gives a stable suspension of the active substance. For FS typecomposition up to 40 wt % binder (e.g. polyvinylalcohol) is added.

-   -   vi) Water-dispersible granules and water-soluble granules (WG,        SG)

50-80 wt % of an benzoxaborole compound of formula (I) according to theinvention are ground finely with addition of dispersants and wettingagents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt %and prepared as water-dispersible or water-soluble granules by means oftechnical appliances (e.g. extrusion, spray tower, fluidized bed).Dilution with water gives a stable dispersion or solution of the activesubstance.

-   -   vii) Water-dispersible powders and water-soluble powders (WP,        SP, WS)

50-80 wt % of an benzoxaborole compound of formula (I) according to theinvention are ground in a rotor-stator mill with addition of 1-5 wt %dispersants (e.g. sodium lignosulfonate), 1-3 wt % wetting agents (e.g.alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt %.Dilution with water gives a stable dispersion or solution of the activesubstance.

-   -   viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt % of an benzoxaborole compound offormula (I) according to the invention are comminuted with addition of3-10 wt % dispersants (e.g. sodium lignosulfonate), 1-5 wt % thickener(e.g. carboxymethylcellulose) and water ad 100 wt % to give a finesuspension of the active substance. Dilution with water gives a stablesuspension of the active substance.

-   -   iv) Microemulsion (ME)

5-20 wt % of an benzoxaborole compound of formula (I) according to theinvention are added to 5-30 wt % organic solvent blend (e.g. fatty aciddimethylamide and cyclohexanone), 10-25 wt % surfactant blend (e.g.alcohol ethoxylate and arylphenol ethoxylate), and water ad 100%. Thismixture is stirred for 1 h to produce spontaneously a thermodynamicallystable microemulsion.

-   -   iv) Microcapsules (CS)

An oil phase comprising 5-50 wt % of an benzoxaborole compound offormula (I) according to the invention, 0-40 wt % water insolubleorganic solvent (e.g. aromatic hydrocarbon), 2-278 wt % acrylic monomers(e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) aredispersed into an aqueous solution of a protective colloid (e.g.polyvinyl alcohol). Radical polymerization initiated by a radicalinitiator results in the formation of poly(meth)acrylate microcapsules.Alternatively, an oil phase comprising 5-50 wt % of an benzoxaborolecompound of formula (I) according to the invention, 0-40 wt % waterinsoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanatemonomer (e.g. diphenylmethene-4,4′-diisocyanate) are dispersed into anaqueous solution of a protective colloid (e.g. polyvinyl alcohol). Theaddition of a polyamine (e.g. hexamethylenediamine) results in theformation of polyurea microcapsules. The monomers amount to 1-10 wt %.The wt % relate to the total CS composition.

-   -   ix) Dustable powders (DP, DS)

1-10 wt % of an benzoxaborole compound of formula (I) according to theinvention are ground finely and mixed intimately with solid carrier(e.g. finely divided kaolin) ad 100 wt %.

-   -   x) Granules (GR, FG)

0.5-30 wt % of an benzoxaborole compound of formula (I) according to theinvention is ground finely and associated with solid carrier (e.g.silicate) ad 100 wt %. Granulation is achieved by extrusion,spray-drying or the fluidized bed.

-   -   xi) Ultra-low volume liquids (UL)

1-50 wt % of an benzoxaborole compound of formula (I) according to theinvention are dissolved in organic solvent (e.g. aromatic hydrocarbon)ad 100 wt %.

The agrochemical compositions types i) to xi) may optionally comprisefurther auxiliaries, such as 0.1-1 wt % bactericides, 5-278 wt %anti-freezing agents, 0.1-1 wt % anti-foaming agents, and 0.1-1 wt %colorants.

The agrochemical compositions generally comprise between 0.01 and 95%,preferably between 0.1 and 90%, and in particular between 0.5 and 75%,by weight of the benzoxaborole compounds of formula (I). Thebenzoxaborole compounds of formula (I) are employed in a purity of from90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

Solutions for seed treatment (LS), suspoemulsions (SE), flowableconcentrates (FS), powders for dry treatment (DS), water-dispersiblepowders for slurry treatment (WS), water-soluble powders (SS), emulsions(ES), emulsifiable concentrates (EC) and gels (GF) are usually employedfor the purposes of treatment of plant propagation materials,particularly seeds. The agrochemical compositions in question give,after two-to-tenfold dilution, active substance concentrations of from0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in theready-to-use preparations. Application can be carried out before orduring sowing.

Methods for applying benzoxaborole compounds of formula (I) oragrochemical compositions thereof, on to plant propagation material,especially seeds, include dressing, coating, pelleting, dusting, soakingand in-furrow application methods of the propagation material.Preferably, compound I or the compositions thereof, respectively, areapplied on to the plant propagation material by a method such thatgermination is not induced, e.g. by seed dressing, pelleting, coatingand dusting.

Various types of oils, wetters, adjuvants, fertilizer, ormicronutrients, and further pesticides (e.g. herbicides, insecticides,fungicides, growth regulators, safeners) may be added to thebenzoxaborole compounds of formula (I) or the agrochemical compositionscomprising them as premix or, if appropriate not until immediately priorto use (tank mix). These agents can be admixed with the agrochemicalcompositions according to the invention in a weight ratio of 1:100 to100:1, preferably 1:10 to 10:1.

The user applies the benzoxaborole compounds of formula (I) according tothe invention or the agrochemical compositions comprising them usuallyfrom a pre-dosage device, a knapsack sprayer, a spray tank, a sprayplane, or an irrigation system. Usually, the agrochemical composition ismade up with water, buffer, and/or further auxiliaries to the desiredapplication concentration and the ready-to-use spray liquor or theagrochemical composition according to the invention is thus obtained.Usually, 20 to 2000 liters, preferably 50 to 400 liters, of theready-to-use spray liquor are applied per hectare of agricultural usefularea.

According to one embodiment, either individual components of theagrochemical composition according to the invention or partiallypremixed components, e.g. components comprising azines of formula (I)may be mixed by the user in a spray tank and further auxiliaries andadditives may be added, if appropriate.

In a further embodiment, individual components of the agrochemicalcomposition according to the invention such as parts of a kit or partsof a binary or ternary mixture may be mixed by the user himself in aspray tank and further auxiliaries may be added, if appropriate.

In a further embodiment, either individual components of theagrochemical composition according to the invention or partiallypremixed components, e.g components comprising benzoxaborole compoundsof formula (I), can be applied jointly (e.g. after tank mix) orconsecutively.

The benzoxaborole compounds of formula (I), are suitable as herbicides.They are suitable as such or as an appropriately formulated composition(agrochemical composition).

The benzoxaborole compounds of formula (I), or the agrochemicalcompositions comprising the azines of formula (I), control vegetation onnon-crop areas very efficiently, especially at high rates ofapplication. They act against broad-leaved weeds and grass weeds incrops such as wheat, rice, maize, soya and cotton without causing anysignificant damage to the crop plants.

This effect is mainly observed at low rates of application.

The benzoxaborole compounds of formula (I), or the agrochemicalcompositions comprising them, are applied to the plants mainly byspraying the leaves or are applied to the soil in which the plant seedshave been sown. Here, the application can be carried out using, forexample, water as carrier by customary spraying techniques using sprayliquor amounts of from about 100 to 1000 I/ha (for example from 300 to400 I/ha). The benzoxaborole compounds of formula (I), or theagrochemical compositions comprising them, may also be applied by thelow-volume or the ultra-low-volume method, or in the form ofmicrogranules.

Application of the benzoxaborole compounds of formula (I), or theagrochemical compositions comprising them, can be done before, duringand/or after the emergence of the undesirable plants.

The benzoxaborole compounds of formula (I), or the agrochemicalcompositions comprising them, can be applied pre-, post-emergence orpre-plant, or together with the seed of a crop plant. It is alsopossible to apply the benzoxaborole compounds of formula (I), or theagrochemical compositions comprising them, by applying seed, pretreatedwith the benzoxaborole compounds of formula (I), or the agrochemicalcompositions comprising them, of a crop plant. If the active ingredientsare less well tolerated by certain crop plants, application techniquesmay be used in which the herbicidal compositions are sprayed, with theaid of the spraying equipment, in such a way that as far as possiblethey do not come into contact with the leaves of the sensitive cropplants, while the active ingredients reach the leaves of undesirableplants growing underneath, or the bare soil surface (post-directed,lay-by).

In a further embodiment, the benzoxaborole compounds of formula (I), orthe agrochemical compositions comprising them, can be applied bytreating seed. The treatment of seeds comprises essentially allprocedures familiar to the person skilled in the art (seed dressing,seed coating, seed dusting, seed soaking, seed film coating, seedmultilayer coating, seed encrusting, seed dripping and seed pelleting)based on the benzoxaborole compounds of formula (I), or the agrochemicalcompositions prepared therefrom. Here, the herbicidal compositions canbe applied diluted or undiluted.

The term “seed” comprises seed of all types, such as, for example,corns, seeds, fruits, tubers, seedlings and similar forms. Here,preferably, the term seed describes corns and seeds. The seed used canbe seed of the useful plants mentioned above, but also the seed oftransgenic plants or plants obtained by customary breeding methods.

When employed in plant protection, the amounts of active substancesapplied, i.e. the benzoxaborole compounds of formula (I), withoutformulation auxiliaries, are, depending on the kind of effect desired,from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, morepreferably from 0.005 to 0.9 kg per ha and in particular from 0.05 to0.5 kg per ha.

In another embodiment of the invention, the application rate of thebenzoxaborole compounds of formula (I) is from 0.001 to 3 kg/ha,preferably from 0.005 to 2.5 kg/ha, of active substance (a.s.).

In another preferred embodiment of the invention, the rates ofapplication of the benzoxaborole compounds of formula (I) according tothe present invention (total amount of benzoxaborole compounds offormula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000g/ha, depending on the control target, the season, the target plants andthe growth stage.

In another preferred embodiment of the invention, the application ratesof the benzoxaborole compounds of formula (I) are in the range from 0.1g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/haor from 5 g/ha to 2000 g/ha.

In another preferred embodiment of the invention, the application rateof the benzoxaborole compounds of formula (I) is 0.1 to 1000 g/ha,preferably 1 to 750 g/ha, more preferably 5 to 500 g/ha.

In treatment of plant propagation materials such as seeds, e.g. bydusting, coating or drenching seed, amounts of active substance of from0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to100 g and most preferably from 5 to 100 g, per 100 kilogram of plantpropagation material (preferably seeds) are generally required.

In another embodiment of the invention, to treat the seed, the amountsof active substances applied, i.e. the benzoxaborole compounds offormula (I) are generally employed in amounts of from 0.001 to 10 kg per100 kg of seed.

When used in the protection of materials or stored products, the amountof active substance applied depends on the kind of application area andon the desired effect. Amounts customarily applied in the protection ofmaterials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of activesubstance per cubic meter of treated material.

Depending on the application method in question, the benzoxaborolecompounds of formula (I), or the agrochemical compositions comprisingthem, can additionally be employed in a further number of crop plantsfor eliminating undesirable plants. Examples of suitable crops are thefollowing:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis,Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa,Brassica napus var. napus, Brassica napus var. napobrassica, Brassicarapa var. silvestris, Brassica oleracea, Brassica nigra, Camelliasinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon,Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica),Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis,Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Heveabrasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglansregia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum,Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisumsativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca,Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre,Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba,Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao,Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Viciafaba, Vitis vinifera and Zea mays.

Preferred crops are Arachis hypogaea, Beta vulgaris spec. altissima,Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrussinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodondactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum,Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeumvulgare, Juglans regia, Lens culinaris, Linum usitatissimum,Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotianatabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus,Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis,Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghumbicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum,Vicia faba, Vitis vinifera and Zea mays.

Especially preferred crops are crops of cereals, corn, soybeans, rice,oilseed rape, cotton, potatoes, peanuts or permanent crops.

The benzoxaborole compounds of formula (I) according to the invention,or the agrochemical compositions comprising them, can also be used ingenetically modified plants. The term “genetically modified plants” isto be understood as plants whose genetic material has been modified bythe use of recombinant DNA techniques to include an inserted sequence ofDNA that is not native to that plant species' genome or to exhibit adeletion of DNA that was native to that species' genome, wherein themodification(s) cannot readily be obtained by cross breeding,mutagenesis or natural recombination alone. Often, a particulargenetically modified plant will be one that has obtained its geneticmodification(s) by inheritance through a natural breeding or propagationprocess from an ancestral plant whose genome was the one directlytreated by use of a recombinant DNA technique. Typically, one or moregenes have been integrated into the genetic material of a geneticallymodified plant in order to improve certain properties of the plant. Suchgenetic modifications also include but are not limited to targetedpost-translational modification of protein(s), oligo- or polypeptides.e.g., by inclusion therein of amino acid mutation(s) that permit,decrease, or promote glycosylation or polymer additions such asprenylation, acetylation farnesylation, or PEG moiety attachment.

Plants that have been modified by breeding, mutagenesis or geneticengineering, e.g. have been rendered tolerant to applications ofspecific classes of herbicides, such as auxin herbicides such as dicambaor 2,4-D; bleacher herbicides such as hydroxyphenylpyruvate dioxygenase(HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactatesynthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones;enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such asglyphosate; glutamine synthetase (GS) inhibitors such as glufosinate;protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitorssuch as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i.e.bromoxynil or ioxynil) herbicides as a result of conventional methods ofbreeding or genetic engineering; furthermore, plants have been maderesistant to multiple classes of herbicides through multiple geneticmodifications, such as resistance to both glyphosate and glufosinate orto both glyphosate and a herbicide from another class such as ALSinhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors.These herbicide resistance technologies are, for example, described inPest Management Science 61, 2005, 246; 61, 2005, 258; 61, 2005, 277; 61,2005, 269; 61, 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57,2009, 108; Australian Journal of Agricultural Research 58, 2007, 708;Science 316, 2007, 1185; and references quoted therein. Severalcultivated plants have been rendered tolerant to herbicides bymutagenesis and conventional methods of breeding, e.g., Clearfield®summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones,e.g., imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerantto sulfonyl ureas, e.g., tribenuron. Genetic engineering methods havebeen used to render cultivated plants such as soybean, cotton, corn,beets and rape, tolerant to herbicides such as glyphosate,imidazolinones and glufosinate, some of which are under development orcommercially available under the brands or trade names RoundupReady®(glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinonetolerant, BASF SE, Germany) and LibertyLink® (glufosinate tolerant,Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more insecticidal proteins,especially those known from the bacterial genus Bacillus, particularlyfrom Bacillus thuringiensis, such as delta-endotoxins, e.g., CryIA(b),CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c;vegetative insecticidal proteins (VIP), e.g., VIP1. VIP2, VIP3 or VIP3A;insecticidal proteins of bacteria colonizing nematodes, e.g.,Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, suchas scorpion toxins, arachnid toxins, wasp toxins, or otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea or barley lectins;agglutinins; proteinase inhibitors, such as trypsin inhibitors, serineprotease inhibitors, patatin, cystatin or papain inhibitors;ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin,luffin, saporin or bryodin; steroid metabolism enzymes, such as3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase,cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ionchannel blockers, such as blockers of sodium or calcium channels;juvenile hormone esterase; diuretic hormone receptors (helicokininreceptors); stilbene synthase, bibenzyl synthase, chitinases orglucanases. In the context of the present invention these insecticidalproteins or toxins are to be understood expressly also as includingpre-toxins, hybrid proteins, truncated or otherwise modified proteins.Hybrid proteins are characterized by a new combination of proteindomains, (see, e.g., WO 02/0278701). Further examples of such toxins orgenetically modified plants capable of synthesizing such toxins aredisclosed, e.g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e.g., in the publicationsmentioned above. These insecticidal proteins contained in thegenetically modified plants impart to the plants producing theseproteins tolerance to harmful pests from all taxonomic groups ofarthropods, especially to beetles (Coeloptera), two-winged insects(Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).Genetically modified plants capable to synthesize one or moreinsecticidal proteins are, e.g., described in the publications mentionedabove, and some of which are commercially available such as YieldGard®(corn cultivars producing the Cry1Ab toxin), YieldGard® Plus (corncultivars producing Cry1Ab and Cry3Bb1 toxins), Starlink® (corncultivars producing the Cry9c toxin), Herculex® RW (corn cultivarsproducing Cry34Ab1, Cry35Ab1 and the enzymePhosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cottoncultivars producing the Cry1Ac toxin), Bollgard® I (cotton cultivarsproducing the Cry1Ac toxin), Bollgard® II (cotton cultivars producingCry1Ac and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing aVIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin);Bt-Xtra®, NatureGard®, KnockOut, BiteGard®, Protecta, Bt11 (e.g.,Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivarsproducing the Cry1Ab toxin and PAT enzyme), MIR604 from Syngenta SeedsSAS, France (corn cultivars producing a modified version of the Cry3Atoxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium(corn cultivars producing the Cry3Bb1 toxin), IPC 531 from MonsantoEurope S.A., Belgium (cotton cultivars producing a modified version ofthe Cry1Ac toxin) and 27807 from Pioneer Overseas Corporation, Belgium(corn cultivars producing the Cry1F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe resistance or tolerance of those plants to bacterial, viral orfungal pathogens. Examples of such proteins are the so-called“pathogenesis-related proteins” (PR proteins, see, e.g., EP-A 392 225),plant disease resistance genes (e.g., potato cultivars, which expressresistance genes acting against Phytophthora infestans derived from theMexican wild potato, Solanum bulbocastanum) or T4-yso-zym (e.g., potatocultivars capable of synthesizing these proteins with increasedresistance against bacteria such as Erwinia amylovora). The methods forproducing such genetically modified plants are generally known to theperson skilled in the art and are described, e.g., in the publicationsmentioned above.

Furthermore, plants are also covered that are by the use of recombinantDNA techniques capable to synthesize one or more proteins to increasethe productivity (e.g., bio-mass production, grain yield, starchcontent, oil content or protein content), tolerance to drought, salinityor other growth-limiting environmental factors or tolerance to pests andfungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of ingredients or newingredients, specifically to improve human or animal nutrition, e.g.,oil crops that produce health-promoting long-chain omega-3 fatty acidsor unsaturated omega-9 fatty acids (e.g., Nexera® rape, DowAgroSciences, Canada).

Furthermore, plants are also covered that contain by the use ofrecombinant DNA techniques a modified amount of ingredients or newingredients, specifically to improve raw material production, e.g.,potatoes that produce increased amounts of amylopectin (e.g. Amflora®potato, BASF SE, Germany).

A further embodiment of the invention is a method of controllingundesired vegetation, which comprises allowing a herbicidally activeamount of at least one compound of formula (I) as defined above to acton plants, their environment or on seed.

The preparation of the benzoxaborole compounds of formula (I) isillustrated by examples; however, the subject matter of the presentinvention is not limited to the examples given.

The products shown below were characterized by the mass ([m/z]) orretention time (RT; [min.]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography-coupled massspectrometry; HPLC column:

RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm;mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1%TFA using a gradient from 5:95 to 100:0 over 5 minutes at 40° C., flowrate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive mode).

The following abbreviations are used:

CH₂Cl₂: Dichloromethane

EtOAc: Acetic acid ethyl ester

THF: Tetrahydrofuran

CH: Cyclohexane

HCl: hydrogen chloride

NaOH: Sodium hydroxyde

DMF: N,N-Dimethylformamide

HPLC: High pressure chromatography

LC: Liquid chromatography

MS: Mass spectrometry

A. PREPARATION EXAMPLES Example 1: Methyl2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-methoxy-acetate(see table below)

0.17 g (1.0 mmol) 5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-ol (CAS1629140-80-2) was dissolved in 8 ml dimethylformamide and 0.41 g (3.0mmol) K2CO3 and 0.22 g (1.2 mmol) 2-bromo-2-methoxyaceticacidmethylesterwere added. After stirring at room temperature for 24 h water was addedand the mixture was extracted with dichloromethane. After evaporation ofthe solvents the residue was chromatographed withdichloromethane/methanol resulting in 30 mg of methyl2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-methoxy-acetateas a colorless oil.

1H-NMR (d6-DMSO): 3.5 (s, 3H); 3.8 (s, 3H); 4.9 (s, 2H); 5.7 (s, 1H);7.4 (d, 1H); 7.6 (d, 1H); 9.3 (s, 1H)

Example 2: Methyl2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-phenyl-acetate(see table below)

0.17 g (1.0 mmol) 5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-ol (CAS1629140-80-2) was dissolved in 8 ml dimethylformamide and 0.41 g (3.0mmol) K2CO3 and 0.28 g (1.2 mmol) 2-bromo-2-phenylaceticacidmethylesterwere added. After stirring at room temperature for 24 h water was addedand the mixture was extracted with ethylacetate. After evaporation ofthe solvents the residue was chromatographed withdichloromethane/methanol resulting in 117 mg of methyl2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-phenyl-acetate asa colorless oil. 1H-NMR (d6-DMSO): 3.7 (s, 3H); 4.9 (s, 2H); 6.0 (s,1H); 7.3-7.6 (m, 5H); 9.3 (s, 1H)

Example 3:2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-phenyl-acetaticacid (see table below)

0.055 g (0.17 mmol) methyl2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-phenyl-acetatewas dissolved in 1 ml isopropanol and 0.35 ml (0.35 mmol) 1M aqueousLiOH-solution was added. After stirring at room temperature for 2 h thesolvents were evaporated, water was added and extracted withdichloromethane. The aqueous phase was acidified with 2N Hcl and theprecipitate filtrated, resulting in 29 mg of2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)oxy]-2-phenyl-acetaticacid as colorless solid.

1H-NMR (d6-DMSO): 4.9 (s, 2H); 5.8 (s, 1H); 7.4-7.6 (m, 5H); 9.3 (s,1H); 13.3 (br, 1H)

The compounds 2 to 3 listed below in Table 3 have been prepared byanalogy to the example 1 mentioned above.

MS-retention time/¹H- NMR(DMSO)/ compound R¹ R² R³ R⁴ R⁵ R⁶ X Y CASnunnber I-1 H H H H H H O —CH₂—  947164-82-1 I-2 H H H H H CH₂ O—C(CH₃)₂— 1268390-39-1 CH₃ I-3 H H H H H CH₃ O —CH₂— 1268390-35-7 I-4 HH H H H H O —C(CH₃)₂— 1296850-35-5 I-5 H H H F H CH₃ O —CH₂—1803546-90-8 I-6 H H H F H H O —CH₂— 0.941 I-7 H H H Cl H CH₃ O —CH₂—1803547-27-4 I-8 H H H Cl H H O —CH₂— 0.956 I-9 H H H Cl Cl CH₃ O —CH₂—1.061 I-10 H H H F H CH₃ O —CH(C═O)(OCH₃)— 1803546-93-1 I-11 H H H F HCH₃ O —CH(OCH₃)— 3.5 (s, 3H); 3.8 (s, 3H); 4.9 (s, 2H); 5.7 (s, 1H); 7.4(d, 1H); 7.6 (d, 1H); 9.3 (s, 1H) I-12 H H H F H CH₃ O —CH(CH₃)₂— 0.898I-13 H H H F H CH₃ O —CH(CH₂CH₃)— 1803546-86-2 I-14 H H H F H CH₃ O—CHPh— 3.7 (s, 3H); 4.9 (s, 2H); 6.0 (s, 1H); 7.3-7.6 (m, 5H); 9.3 (s,1H) I-15 H H H Cl Cl H O —CH₂— 0.98 I-16 H H H F H H O —CHPh— 4.9 (s,2H); 5.8 (s, 1H); 7.4-7.6 (m, 5H); 9.3 (s, 1H); 13.3 (br, 1H) I-17 H H HH H CH₃ NH —CH₂— 0.703 I-18 CH₃ H H H H H O —CH₂— 0.723 I-19 H H H H HCH₃ NCH₃ —CH₂— 0.785 I-20 CH₃ H H H H CH₃ O —CH₂— 0.858 I-21 H H H F H HO —(CH₂)₂— 0.748 I-22 H H H F H H S —CH₂— 0.931 I-23 H H F F H H O —CH₂—0.861 I-24 H H H F F H O —CH₂— 0.852 I-25 H H H F H H O —(CH₂)₃— 0.779I-26 H H H H H CH₂ O —CHF— 0.919 CH₃ I-27 CH₃ H H F H CH₃ O —CH₂— 0.908I-28 H H H F H CH₃ S —CH₂— 0.955 I-29 H H H F F CH₃ O —CH₂— 0.893 I-30 HH H F F H O —CHCH₃— 0.894 I-31 H H F F H CH₃ O —CH₂— 0.891 I-32 H H Cl FH H O —CH₂— 0.903 I-33 H H F F F H O —CH₂— 0.875 I-34 H H H F H CH₂ O—CHF— 0.963 CH₃ I-35 H H H F F CH₃ O —CHCH₃— 0.955 I-36 CH₃ H F F H CH₃O —CH₂— 0.96 I-37 H H H F H H SO₂ —CH₂— 0.755 I-38 H H Cl F H CH₃ O—CH₂— 1.078 I-39 H H F F F CH₃ O —CH₂— 0.97 I-40 H H H F H CH₂ O—(CH₂)₃— 1.007 CH₃ I-41 CH₂ H F F H CH₃ O —CH₂— 1.019 CH₃ I-42 H H H F HCH₃ SO₂ —CH₂— 0.809

B USE EXAMPLES

The herbicidal activity of the azines of formula (I) was demonstrated bythe following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamysand with approximately 3.0% of humus as the substrate. The seeds of thetest plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had beensuspended or emulsified in water, were applied directly after sowing bymeans of finely distributing nozzles. The containers were irrigatedgently to promote germination and growth and subsequently covered withtransparent plastic hoods until the plants had rooted. This cover causeduniform germination of the test plants, unless this had been impaired bythe active ingredients.

For the post-emergence treatment, the test plants were first grown to aheight of 3 to 8 cm, depending on the plant habit, and only then treatedwith the active ingredients which had been suspended or emulsified inwater. For this purpose, the test plants were either sown directly andgrown in the same containers, or they were first grown separately asseedlings and transplanted into the test containers a few days prior totreatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35°C., respectively.

The test period extended over 2 to 4 weeks. During this time, the plantswere tended, and their response to the individual treatments wasevaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means noemergence of the plants, or complete destruction of at least the aerialmoieties, and 0 means no damage, or normal course of growth. A moderateherbicidal activity is given at values of at least 60, a good herbicidalactivity is given at values of at least 70, and a very good herbicidalactivity is given at values of at least 85.

The plants used in the greenhouse experiments were of the followingspecies:

Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopecurusmyosuroides AMARE Amaranthus retroflexus AVEFA Avena fatua ECHCGEchinocloa crus-galli SETVI Setaria viridis

The results of the herbicidal activity of compounds I against variousweed species and certain monocot crop plants at different applicationrates are summarized in Examples 1-10 below.

Example 1

At an application rate of 2 kg/ha, the compound I-1 applied by thepost-emergence method, showed 100%, 90%, 100%, 90% and 100% herbicidalactivity against Echinocloa crus-galli, Abutilon theophrasti, Amaranthusretroflexus, Avena fatua and Setaria viridis respectively.

Example 2

At an application rate of 2 kg/ha, the compound I-2 applied by thepost-emergence method, showed 100% herbicidal activity againstAmaranthus retroflexus.

Example 3

At an application rate of 2 kg/ha, the compound I-3 applied by thepost-emergence method, showed 98%, 100%, 100% 90% and 100% herbicidalactivity against Echinocloa crus-galli, Abutilon theophrasti, Amaranthusretroflexus, Avena fatua and Setaria viridis respectively.

Example 4

At an application rate of 2 kg/ha, the compound I-5 applied by thepost-emergence method, showed 98%, 98%, 100%, 100%, 98% and 98%herbicidal activity against Echinocloa crus-galli, Alopecurusmyosuroides, Abutilon theophrasti, Amaranthus retroflexus, Avena fatuaand Setaria viridis respectively.

Example 5

At an application rate of 2 kg/ha, the compound I-6 applied by thepost-emergence method, showed 98%, 90%, 100%, 100%, 98% and 100%herbicidal activity against Echinocloa crus-galli, Alopecurusmyosuroides, Abutilon theophrasti, Amaranthus retroflexus, Avena fatuaand Setaria viridis respectively.

Example 6

At an application rate of 2 kg/ha, the compound 1-7 applied by thepost-emergence method, showed 100%, 95%, 100%, 100%, 98% and 100%herbicidal activity against Echinocloa crus-galli, Alopecurusmyosuroides, Abutilon theophrasti, Amaranthus retroflexus, Avena fatuaand Setaria viridis respectively.

Example 7

At an application rate of 2 kg/ha, the compound 1-8 applied by thepost-emergence method, showed 100%, 98%, 100%, 100%, 98% and 95%herbicidal activity against Echinocloa crus-galli, Alopecurusmyosuroides, Abutilon theophrasti, Amaranthus retroflexus, Avena fatuaand Setaria viridis respectively.

Example 8

At an application rate of 2 kg/ha, the compound 1-10 applied by thepost-emergence method, showed 90% and 95% herbicidal activity againstAmaranthus retroflexus and Setaria viridis respectively.

Example 9

At an application rate of 2 kg/ha, the compound 1-15 applied by thepost-emergence method, showed 85%, 100% and 90% herbicidal activityagainst Echinocloa crus-galli, Amaranthus retroflexus and Setariaviridis respectively.

Example 10

At an application rate of 2 kg/ha, the compound 1-4 applied by thepost-emergence method, showed 85% herbicidal activity against Echinocloacrus-galli and Abutilon theophrasti.

Example 11

At an application rate of 2 kg/ha, the compound 1-39 applied by thepost-emergence method, showed 100% herbicidal activity againstAmaranthus retroflexus and Setaria viridis.

Example 12

At an application rate of 2 kg/ha, the compound 1-25 applied by thepost-emergence method, showed 95% herbicidal activity against Amaranthusretroflexus and Setaria viridis.

Example 13

At an application rate of 2 kg/ha, the compound 1-28 applied by thepost-emergence method, showed 100% herbicidal activity against Abutilontheophrasti, Amaranthus retroflexus and Setaria viridis.

Example 14

At an application rate of 2 kg/ha, the compound 1-42 applied by thepost-emergence method, showed 100% herbicidal activity against Abutilontheophrasti and Amaranthus retroflexus.

Example 15

At an application rate of 2 kg/ha, the compound 1-33 applied by thepost-emergence method, showed 98%, 100% and 98% herbicidal activityagainst Abutilon theophrasti, Amaranthus retroflexus and Setaria viridisrespectively.

Example 16

At an application rate of 2 kg/ha, the compound 1-22 applied by thepost-emergence method, showed 100% herbicidal activity against Abutilontheophrasti, Amaranthus retroflexus and Setaria viridis.

Example 17

At an application rate of 2 kg/ha, the compound 1-37 applied by thepost-emergence method, showed 100% herbicidal activity againstAmaranthus retroflexus.

Example 18

At an application rate of 2 kg/ha, the compound 1-29 applied by thepost-emergence method, showed 95%, 100% and 100% herbicidal activityagainst Echinocloa crus-galli, Amaranthus retroflexus, Setaria viridisrespectively.

Example 19

At an application rate of 2 kg/ha, the compound 1-26 applied by thepost-emergence method, showed 90%, 100% and 85% herbicidal activityagainst Abutilon theophrasti, Amaranthus retroflexus and Setaria viridisrespectively.

Example 20

At an application rate of 2 kg/ha, the compound 1-35 applied by thepost-emergence method, showed 100%, 100% and 98% herbicidal activityagainst Abutilon theophrasti, Amaranthus retroflexus and Setaria viridisrespectively.

Example 21

At an application rate of 2 kg/ha, the compound 1-24 applied by thepost-emergence method, showed 100%, 100% and 95% herbicidal activityagainst Abutilon theophrasti, Amaranthus retroflexus and Setaria viridisrespectively.

Example 22

At an application rate of 2 kg/ha, the compound 1-30 applied by thepost-emergence method, showed 85%, 95% and 100% herbicidal activityagainst Alopecurus myosuroides, Abutilon theophrasti and Amaranthusretroflexus respectively.

1-15. (canceled)
 16. A method for controlling unwanted vegetation,wherein the unwanted vegetation, their seed, and/or their habitat istreated with a herbicidally effective amount of the compound of formulaI

wherein X is O, NR⁷ or S, SO, SO₂; Y is selected from the groupconsisting of C₁-C₆-alkyl, C₃-C₆-alkenyl, and C₃-C₆-alkynyl wherein theradicals are unsubstituted or substituted by 1, 2, 3, 4 or 5 identicalor different substituents selected from the group consisting of halogen,C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy,C(═O)O(C₁-C₆-alkyl) and phenyl which is unsubstituted or substituted byhalogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl; R¹ is selected from the groupconsisting of H and C₁-C₆-alkyl; R² is selected from the groupconsisting of H and C₁-C₆-alkyl; R³ is selected from the groupconsisting of H, halogen, OH, CN, amino, NO₂, C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy, C₂-C₆-alkenyloxy,C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,(C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, and(C₁-C₆-alkoxy)-C₃-C₆-alkynyl, wherein the aliphatic parts of theaforementioned radicals are unsubstituted, partly or completelyhalogenated; R⁴ is selected from the group consisting of H, halogen, OH,CN, amino, NO₂, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,(C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, and(C₁-C₆-alkoxy)-C₃-C₆-alkynyl, wherein the aliphatic parts of theaforementioned radicals are unsubstituted, partly or completelyhalogenated; R⁵ is selected from the group consisting of H, halogen, OH,CN, amino, NO₂, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₁-C₆-alkoxy,C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,(C₁-C₆-alkoxy)-C₁-C₆-alkoxy, (C₁-C₆-alkoxy)-C₃-C₆-alkenyl, and(C₁-C₆-alkoxy)-C₃-C₆-alkynyl, wherein the aliphatic parts of theaforementioned radicals are unsubstituted, partly or completelyhalogenated; R⁶ is selected from the group consisting of H, C₁-C₆-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkynyl, (C₁-C₆-alkoxy)-C₁-C₆-alkyl,(C₁-C₆-alkoxy)-C₃-C₆-alkenyl, (C₁-C₆-alkoxy)-C₃-C₆-alkynyl, phenyl, andphenyl-C₁-C₆-alkyl, wherein the aliphatic and phenyl parts of theaforementioned radicals are unsubstituted, partly or completelyhalogenated; R⁷ is selected from the group consisting of H, C₁-C₆-alkyl,C₃-C₆-alkenyl, and C₃-C₆-alkynyl; or an agriculturally suitable salt orN-oxide thereof.
 17. The method of claim 16, wherein X is O.
 18. Themethod of claim 16, wherein Y is C₁-C₆-alkyl which is unsubstituted. 19.The method of claim 16, wherein Y is —CH₂—.
 20. The method of claim 16,wherein Y is C₁-C₆-alkyl which is substituted by 1 or 2 identical ordifferent substituents selected from the group consisting ofC₁-C₆-alkyl, C₁-C₆-alkoxy, C(═O)O(C₁-C₆-alkyl) and phenyl.
 21. Themethod of claim 20, wherein Y is —CH₂— which is substituted by 1 or 2identical or different substituents selected from the group consistingof CH₃, CH₂CH₃, C(═O)(OCH₃), OCH₃ and unsubstituted phenyl.
 22. Themethod of claim 16, wherein R¹ and R² are independently selected fromthe group consisting of H and C₁-C₄-alkyl.
 23. The method of claim 16,wherein R³ is selected from the group consisting of H, halogen,C₁-C₆-alkyl and C₁-C₆-haloalkyl.
 24. The method of claim 16, wherein R⁴is selected from the group consisting of H, halogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl.
 25. The method of claim 16, wherein R⁵ is selected fromthe group consisting of H, halogen, C₁-C₆-alkyl and C₁-C₆-haloalkyl. 26.The method of claim 16, wherein R⁶ is selected from the group consistingof H and C₁-C₆-alkyl.
 27. The method of claim 16, wherein R⁶ is H and R⁴is selected from the group consisting of halogen, C₁-C₆-alkyl andC₁-C₆-haloalkyl.
 28. The compound of the formula (I) as defined in claim16

with the proviso that if R¹ and R² are H R⁴ is not H, Cl and F; and ifR¹ or R² is CH₃ R⁴ is not H.
 29. An agrochemical composition comprisinga herbicidal active amount of at least one compound as claimed in claim16 and at least one inert liquid and/or solid carrier and, ifappropriate, at least one surface-active substances.
 30. The method ofclaim 22, wherein R¹ and R² are both H.
 31. The method of claim 23,wherein R³ is H.
 32. The method of claim 24, wherein R⁴ is selected fromthe group consisting of H, Cl, and F.
 33. The method of claim 25,wherein R⁵ is selected from the group consisting of H, Cl, and F. 34.The method of claim 26, wherein R⁶ is selected from the group consistingof H, CH₃, and CH₂CH₃.
 35. The method of claim 27, wherein R⁴ isselected from the group consisting of Cl and F.